Personalized care for your dog or cat - Oakwood

Highly-rated overnight sitters - Oakwood

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Shuling J.
Verified Enhanced Background Check
Shuling J.
Star Sitter
from
$45
per night
5.0 out of 5 stars
143 reviews
65 repeat clients
8 years of experience
Annapolis, MD, 21401

We are very pleased with Shuling as she is very friendly and easy to work with. Our dog gets excited when we arrive at her house. Leia runs to her front door without even looking back to see where we are.

Profile image
Lynn C.
Sitter Profile Image: Shelby B.
Verified Enhanced Background Check
Shelby B.
from
$57
per night
5.0 out of 5 stars
24 reviews
5 repeat clients
7 years of experience
Annapolis, MD, 21403

Moose had the best weekend with Shelby and her pup! It’s always nerve wracking when you leave your pet for the weekend but Shelby made us feel so comfortable by sending photos and treating Moose like her own. Highly recommend her to watch your fur baby!

Profile image
Samantha P.
Sitter Profile Image: Michelle M.
Verified Background Check
Michelle M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
556 reviews
257 repeat clients
25 years of experience
Annapolis, MD, 21409

Michelle has been caring for our dog, Lucy, for years now... and we have been nothing but pleased with her loving care for Lucy, her great communication, and dependability. Lucy loves her vacations with Michelle, and we always feel 100% confident in the care we know she will receive. Definitely 5 stars in every area!

Profile image
Mollie M.
Sitter Profile Image: Stacia D.
Verified Enhanced Background Check
Stacia D.
from
$60
per night
12 years of experience
Annapolis, MD, 21403

About: Hi there! My name is Stacia and I’ve taken care of animals my whole life. I am a dog owner too! Remi is a 2 years old, playful, dark yellow lab. He is fixed. I’m familiar with ensuring the environment is right for your dog. I previously owned a dog with high anxiety and wasn’t friendly with strangers. I understand the importance of making sure your guidelines for your pet are followed. I can give oral medications, follow your training rules, walk large dogs, handle dogs that aren’t friendly with strangers, high anxiety, and have disabilities (ex. Deaf, blind). These dogs are our best friends so I promise to take great care of yours :) If you have any additional questions for me, please don’t hesitate to ask. I am happy to chat or meet prior to booking to ensure I am a good fit for your pup! I believe in open communication to ensure the safety of you, your pet, me and mine. I work fully remote and am able to support daycare and boarding. I usually walk my dog morning, mid day and evening for 30 min to an hour at a time. I’d like to be able to support other people who need assistance. During the week your dog won’t be left alone for more than an hour depending on drop off and pick up time. During the weekend your dog won’t be left longer than 3-4 hours depending. We can always communicate your dogs specific needs to accommodate! I have a fenced yard in our home and a friendly, playful 2 year old male lab (fixed). If your dog is in my home, they do need to be friendly with other dogs. During the week I do work full time so there are times where I am in meetings so it is preferred your dog is not destructive or is okay in a crate or enclosed room during meetings. I do make sure the dogs are exercised before and after. I communicate my anticipated work schedule and plan for the day with the pet owner.

Sitter Profile Image: Carlie H.
Verified Enhanced Background Check
Carlie H.
Star Sitter
from
$45
per night
5.0 out of 5 stars
69 reviews
29 repeat clients
15 years of experience
Severna Park, MD, 21146

After a meet and greet we decided to do an overnight trial and our dog loved it! The whole family is very warm and inviting and our dog felt at home the moment he walked in the door. Their house has a nice fenced in backyard as a plus. We have already booked our summer vacation and plan on booking other trips as well. Very happy to have found such a perfect fit.

Profile image
Kathy T.
Sitter Profile Image: Katelyn M.
Verified Background Check
Katelyn M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
87 reviews
24 repeat clients
8 years of experience
Arnold, MD, 21012

This was our first experience with Rover and it was absolutely wonderful! We have an older dog and she is both blind and deaf and Katelyn took such good care of her. She welcomed her into her home and treated her as if she were her own. Her communication was great. We received pictures/videos/updates several times a day. We will definitely use Katelyn again and highly recommend her!

Profile image
Eileen Or Jack S.
Sitter Profile Image: Megan T.
Verified Enhanced Background Check
Megan T.
from
$33
per night
5.0 out of 5 stars
5 reviews
1 repeat client
4 years of experience
Annapolis, MD, 21403

Meghan is easy to work with and super accommodating. Gave my girl, Aurora, lots of exercise and TLC. We loved our stay with her!

Profile image
Rob C.
Sitter Profile Image: Katie F.
Verified Enhanced Background Check
Katie F.
from
$55
per night
5.0 out of 5 stars
114 reviews
36 repeat clients
16 years of experience
Annapolis, MD, 21401

Katie was amazing with my dog! She was flexible on drop off and pickup. She also sent many pictures to jeep us updated. She treated her like one of her own pups. My dog did not want to leave!

Profile image
Michael F.
Sitter Profile Image: James B.
Verified Enhanced Background Check
James B.
from
$40
per night
30 years of experience
Annapolis, MD, 21403

About: I've had dogs my whole life. Grew up in a house with 2+ dogs near constantly. All family dogs were 60+ lbs each with the largest being 110lbs. My 75lb dog crossed the rainbow bridge Sept 2025, I am not ready for a dog full time but I do miss the company. I will spoil your dog. I do not care about breed. I am looking for weekends. I work full time, so I am ready to go around noon on Friday and depending on the needs can be around all weekend. Generally I do leave the house during the weekend for a couple hours during the day to do chores and stuff but other than that can be a total home body. If the dog is good on leash I have a great neighborhood to take walks. If you are looking for me to stay at your house over the weekend, I can provide as much potty coverage as you request. If you want me to stay over the week, I do have a day job with my schedule being 7-3. I have a 8ft privacy fence the whole way around my backyard with a dog door. I do not have a crate, but I can use yours if you want your dog crated. I follow your food rules. I used to make hot breakfast/dinner for my dog. I do keep some dog treats in the house but I will check with you if your dog can have that specific treat first and if there are any dietary needs. If you want me to stay in your house, lets write the rules down and I'm happy to do whatever. If you have poor cellphone service, it'd be great to get a wifi password.

Sitter Profile Image: Elaine S.
Verified Background Check
Elaine S.
from
$50
per night
5.0 out of 5 stars
69 reviews
37 repeat clients
20 years of experience
Annapolis, MD, 21403

I wholeheartedly recommend Elaine, and am grateful for her dependability, flexibility, and all the care she provided our dog when she stayed at Elaine's home. Will definitely be a return visitor!

Profile image
Marlys M.
Sitter Profile Image: Thomas & Melissa S.
Verified Background Check
Thomas & Melissa S.
from
$60
per night
5.0 out of 5 stars
38 reviews
14 repeat clients
7 years of experience
Annapolis, MD, 21403

Trey and Melissa treated Abby like their own dog! They had great communication throughout the process and sent pictures and videos while we were away. We definitely recommended them!

Profile image
Kate D.
Sitter Profile Image: Ashley H.
Verified Background Check
Ashley H.
from
$40
per night
4.9 out of 5 stars
28 reviews
8 repeat clients
25 years of experience
Annapolis, MD, 21403

Ashley was an absolute lifesaver! She came to our rescue at the last minute, and took excellent care of my Rebel. Ashley sent pictures everyday, and Rebel came home a happy boy.

Profile image
Tracie M.
Sitter Profile Image: Tiffany C.
Verified Enhanced Background Check
Tiffany C.
from
$40
per night
5.0 out of 5 stars
5 reviews
1 repeat client
40 years of experience
Edgewater, MD, 21037

We thought we were having a good time until Tiffany sent pictures of our dogs. They were having the time of their lives! Tiffany is so kind and caring. She sent pictures of both dogs, cooked them food, let them sleep where they were comfortable. I couldn’t have picked a better person, and I will now only allow them to stay with Tiffany. Wonderful experience and big thanks to Tiffany!

Profile image
Stacy G.
Sitter Profile Image: Diana V.
Verified Enhanced Background Check
Diana V.
Star Sitter
from
$57
per night
5.0 out of 5 stars
206 reviews
90 repeat clients
10 years of experience
Riva, MD, 21140

Diana did an excellent job with my Kingston. He is very sweet, and loves to cuddle but gets anxious when we are separated. Diana was caring and kind to Kingston, spent a lot of time with him, and sent plenty of pictures. Great sitter!

Profile image
Regina J.
Sitter Profile Image: Celena W.
Verified Enhanced Background Check
Celena W.
Star Sitter
from
$45
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
4 years of experience
Annapolis, MD, 21409

Celena was great! She sent tons pictures of our boy having a great time and she had plenty of updates. We also appreciate that she worked with us on our drop-off and pick-up times! We will definitely work with her again!

Profile image
Katie J.
Sitter Profile Image: Beth H.
Verified Enhanced Background Check
Beth H.
Star Sitter
from
$68
per night
5.0 out of 5 stars
56 reviews
17 repeat clients
40 years of experience
Edgewater, MD, 21037

Beth is simply the best! She has provided loving and professional care to both our late geriatric Shih Tzu who had a number of health issues AND our new 5 month old Havanese puppy. Both dogs loved her! We have such confidence in Beth that whenever we need to go away, we can do so with confidence knowing our pup will enjoy her "vacation" too! We appreciate Beth so much and could not recommend her more highly.

Profile image
Robin S.
Sitter Profile Image: Jessica B.
Verified Enhanced Background Check
Jessica B.
from
$53
per night
5.0 out of 5 stars
39 reviews
11 repeat clients
20 years of experience
annapolis, MD, 21403

Jessica was great with our Remmie. She asked all the right questions ahead of time, and during the stay we received regular photos and updates. Will definitely want to have our girl visit again.

Profile image
Tim W.
Sitter Profile Image: Emily S.
Verified Enhanced Background Check
Emily S.
from
$60
per night
5.0 out of 5 stars
13 reviews
5 repeat clients
10 years of experience
Annapolis, MD, 21403

Emily was a fantastic sitter for Rudy! This was our first time with Emily and Rover and the experience was all positive. Emily kept in daily contact sending brief texts and/or pictures of Rudy that truly set my mind at ease during this first visit. Rudy also enjoyed playing with Emily's dogs, Pumpkin and Scooter. We would definitely use Emily again!

Profile image
Tracey B.
Sitter Profile Image: Anya B.
Verified Enhanced Background Check
Anya B.
from
$25
per night
8 years of experience
North Beach, Annapolis, MD, 21401

About: I have grown up with medium to large sized dogs my whole life. I have experience with very friendly dogs and dogs that cannot play with others as well as puppies to older dogs. I have cared for my own pets and friends while growing up and can be trusted with any task to ensure your pets needs and safety! I can offer dog walking in the mornings (7-9am) or afternoons (4-7pm) during the week or anytime during the weekends. I am available on the weekends to check-in or stay with your animal overnight as well. I can check-in and care for your animal during the day or overnight at clients homes. I will ensure your pet is fed, walked, bathed, played with and let outside for their needs. I am comfortable with any specific instructions from the owners as well (medication that needs to be taken, crate training, etc).

Sitter Profile Image: Lucy & Daniel M.
Verified Enhanced Background Check
Lucy & Daniel M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
17 reviews
4 repeat clients
15 years of experience
Annapolis, MD, 21403

Appreciate Lucy and Daniel so much, they did a wonderful job with our pup. Provided updates and were very communicative throughout booking and the stay, would absolutely trust them to watch our boy anytime.

Profile image
Hassie C.
1 / 1
View more sitters

Over 4.1 million
dogs curled up for a sleepover in a sitter's home on Rover1

Cat caregivers near you - Oakwood

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Katie B.
Verified Enhanced Background Check
Katie B.
from
$20
per visit
5.0 out of 5 stars
34 reviews
8 repeat clients
37 years of experience
Annapolis, MD, 21403

Katie took extra care with my shy cats, and made sure to give everyone lots of cuddle and play time. I felt very comfortable while I was away. Will definitely use her services again!

Profile image
Michael W.
Sitter Profile Image: Ellie H.
Verified Enhanced Background Check
Ellie H.
from
$13
per visit
5.0 out of 5 stars
10 reviews
3 repeat clients
10 years of experience
Annapolis, MD, 21403

Ellie did a great job with our dog Piggy! She was able to accept the booking last minute, showed up as scheduled and sent us photos and updates that showed us how happy Piggy was with her care. We would definitely book her again! Thanks Ellie!!

Profile image
Joan D.
Sitter Profile Image: Leigh Ann E.
Verified Enhanced Background Check
Leigh Ann E.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
15 reviews
5 repeat clients
37 years of experience
Annapolis, MD, 21403

10/10 - without a doubt my go-to sitter

Profile image
Noah M.
Sitter Profile Image: Lucille F.
Verified Enhanced Background Check
Lucille F.
from
$23
per visit
4 years of experience
Annapolis, MD, 21403

About: During my time as a pet attendant, I spent much of my time handling the cats' daily feedings, cleaning the homes, and making sure any medications were administered correctly per the owners' instructions. Additionally, I enjoy researching and understanding how to identify and understand cats' behavior to best cater to their individual needs. Finally, I have participated in many sitting opportunities for friends or family that required overnight stays, medication administration, and maintaining the needs of the cats' physical and mental enrichment. Overall, my job is making sure that your feline has the best time while you are out of town:)

Sitter Profile Image: Elaine S.
Verified Background Check
Elaine S.
from
$18
per visit
5.0 out of 5 stars
69 reviews
37 repeat clients
20 years of experience
Annapolis, MD, 21403

About: I get a lot of pleasure assisting busy professionals with their pet sitting needs. I provide a nurturing and loving environment for your special pets in a very tranquil setting. Your pets will be treated as if they were my own. My husband and I will treat your pet with the utmost care and attention. References available upon request.

Sitter Profile Image: Elizabeth G.
Verified Enhanced Background Check
Elizabeth G.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
45 reviews
21 repeat clients
12 years of experience
Annapolis, MD, 21403

Elizabeth did a wonderful caring for my cats while I was away! She sent photos of them and let me know their antics (rearranging my carpets with their zoomies). Very easy to work with

Profile image
Mary Beth P.
Sitter Profile Image: Laura D.
Verified Enhanced Background Check
Laura D.
Star Sitter
from
$24
per visit
5.0 out of 5 stars
59 reviews
19 repeat clients
35 years of experience
Annapolis, MD, 21403

Laura did a wonderful job taking care of my cat Ollie. She went above and beyond by buying new toys for him to play with to keep him engaged and active during her visits. She accommodated a last minute extension of my trip, covering the additional days. She also handled a mishap when Ollie broke into his food and made a mess, cleaning everything up. She provided detailed Rover cards with lots of photos. She took the time to get to know Ollie and developed a good relationship with him. I was able to enjoy my trip knowing Ollie was well taken care of. I will definitely book Laura again!

Profile image
Stan W.
Sitter Profile Image: Stella N.
Verified Enhanced Background Check
Stella N.
from
$20
per visit
5.0 out of 5 stars
15 reviews
3 repeat clients
7 years of experience
Annapolis, MD, 21403

Stella did a great job checking in on our cat! She was communicative and punctual.

Profile image
Lauren G.
Sitter Profile Image: Beth W.
Verified Enhanced Background Check
Beth W.
Star Sitter
from
$26
per visit
5.0 out of 5 stars
72 reviews
32 repeat clients
25 years of experience
Annapolis, MD, 21403

Beth did a great job with my boys! She coaxed my reticent kitties to come out from under the bed and gave them much love in addition to food and water. Knowing my cats were being well cared for made me feel at ease and able to enjoy my time away from my home and from my boys. Thank you, Beth!

Profile image
Katy S.
Sitter Profile Image: Taylor C.
Verified Enhanced Background Check
Taylor C.
from
$30
per visit
5.0 out of 5 stars
172 reviews
53 repeat clients
12 years of experience
Annapolis, MD, 21403

I’m a happy repeat customer of Taylor and highly recommend her! She recently took great care of our cat for 7 days of drop-in visits. Her attention to detail and frequent communication set us at ease while we were away.

Profile image
Tanya L.
Sitter Profile Image: Andrew P.
Verified Enhanced Background Check
Andrew P.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
66 reviews
19 repeat clients
1 year of experience
Annapolis, MD, 21403

I highly recommend Andrew for any pet sitting needs! He checked in on my cat and provided timely updates & great photos! Very responsive & communicative too!!

Profile image
Alex P.
Sitter Profile Image: Katherine V.
Verified Enhanced Background Check
Katherine V.
from
$18
per visit
15 years of experience
Annapolis, MD, 21403

About: Cats deserve just as much attention and care while their owners are away. I’m happy to provide: Feeding and water refresh Litter box cleaning Playtime and enrichment Medication assistance if needed Quiet companionship for shy cats Daily updates and photos

Sitter Profile Image: Heather B.
Verified Background Check
Heather B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
157 reviews
51 repeat clients
17 years of experience
Annapolis, MD, 21401

Heather took care of my two kitties and did an amazing job! She followed all the instructions for their feeding schedules and kept the litter boxes clean. I look forward to working with her in the future!

Profile image
January K.
Sitter Profile Image: Mary H.
Verified Enhanced Background Check
Mary H.
from
$20
per visit
5.0 out of 5 stars
5 reviews
2 years of experience
Annapolis, MD, 21403

About: I have experience caring for cats, including feeding, play time, and litter changes. I would love to help you with caring for your kitty while you’re away!

Sitter Profile Image: Harrison S.
Verified Enhanced Background Check
Harrison S.
from
$14
per visit
3 repeat clients
6 years of experience
Annapolis, MD, 21403

About: I have had my cat ever since I was a kid I have trained my cat to stay close to home, to sit and too be friendly to other people that he meets.

Sitter Profile Image: Amanda S.
Verified Enhanced Background Check
Amanda S.
from
$15
per visit
5.0 out of 5 stars
3 reviews
4 repeat clients
12 years of experience
Edgewater, MD, 21037

Definitely took great care of my dog Rocco. Would definitely rebook!

Profile image
Vincent J R.
Sitter Profile Image: Courtney A.
Verified Background Check
Courtney A.
Star Sitter
from
$26
per visit
5.0 out of 5 stars
15 reviews
4 repeat clients
15 years of experience
Edgewater, MD, 21037

My cats love Courtney! Especially my super shy boy comes out of shell when he sees her. I’m super happy with her taking care of my two little ones, she spends quality time with them and doesn’t cut her visits short. I also really appreciate the detailed write up and the cute photos. Thank you, Courtney!

Profile image
Anne-Katrin A.
Sitter Profile Image: Kathryn U.
Verified Enhanced Background Check
Kathryn U.
from
$13
per visit
5.0 out of 5 stars
19 reviews
4 repeat clients
16 years of experience
Annapolis, MD, 21401

Kathryn came and watched my Baby Boy on a very last minute notice and as always, did a wonderful job. Kathryn was exceptionally accommodating and really helped out in a tight spot. I will most definitely be requesting Kathryn in the future.

Profile image
Robyn R.
Sitter Profile Image: Halsey C.
Verified Enhanced Background Check
Halsey C.
from
$20
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
3 years of experience
Annapolis, MD, 21403

Halsey did a great job of taking care of my cat Toby, would definitely hire her again for drop-ins! He was well-loved during a short trip while I was away.

Profile image
Sophia C.
Sitter Profile Image: Blinne F.
Verified Enhanced Background Check
Blinne F.
from
$18
per visit
5.0 out of 5 stars
20 reviews
6 repeat clients
20 years of experience
Annapolis, MD, 21403

Blinne was great with my pup, she went on long walks, my dog loved her, & she even did some training with her! I would definitely book with her again!

Profile image
Victoria E.
1 / 1
View more sitters

Why choose a sitter on Rover

  • Background-checked house sitters

    Every sitter profile has been reviewed and approved by Rover before joining our community.

  • A perfect match for every pet

    Read sitter profiles to find 5-star reviews and specialists who understand your pet's unique personality.

  • Connection before booking

    Schedule a free in-person meeting to ensure a perfect fit before you ever book.

Perfect for high energy dogs - Oakwood

Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Stacia D.
Verified Enhanced Background Check
Stacia D.
from
$45
per day
12 years of experience
Annapolis, MD, 21403

About: Hi there! My name is Stacia and I’ve taken care of animals my whole life. I am a dog owner too! Remi is a 2 years old, playful, dark yellow lab. He is fixed. I’m familiar with ensuring the environment is right for your dog. I previously owned a dog with high anxiety and wasn’t friendly with strangers. I understand the importance of making sure your guidelines for your pet are followed. I can give oral medications, follow your training rules, walk large dogs, handle dogs that aren’t friendly with strangers, high anxiety, and have disabilities (ex. Deaf, blind). These dogs are our best friends so I promise to take great care of yours :) If you have any additional questions for me, please don’t hesitate to ask. I am happy to chat or meet prior to booking to ensure I am a good fit for your pup! I believe in open communication to ensure the safety of you, your pet, me and mine. I work fully remote and am able to support daycare and boarding. I usually walk my dog morning, mid day and evening for 30 min to an hour at a time. I’d like to be able to support other people who need assistance. During the week your dog won’t be left alone for more than an hour depending on drop off and pick up time. During the weekend your dog won’t be left longer than 3-4 hours depending. We can always communicate your dogs specific needs to accommodate! I have a fenced yard in our home and a friendly, playful 2 year old male lab (fixed). If your dog is in my home, they do need to be friendly with other dogs. During the week I do work full time so there are times where I am in meetings so it is preferred your dog is not destructive or is okay in a crate or enclosed room during meetings. I do make sure the dogs are exercised before and after. I communicate my anticipated work schedule and plan for the day with the pet owner.

Sitter Profile Image: Taylor C.
Verified Enhanced Background Check
Taylor C.
from
$60
per day
5.0 out of 5 stars
172 reviews
53 repeat clients
12 years of experience
Annapolis, MD, 21403

Taylor took such great care of Millie, she was super attentive, caring and kept me updated with how she was doing! I'll definitely be using her services again!

Profile image
Morgan W.
Sitter Profile Image: Lucy & Daniel M.
Verified Enhanced Background Check
Lucy & Daniel M.
Star Sitter
from
$40
per day
5.0 out of 5 stars
17 reviews
4 repeat clients
15 years of experience
Annapolis, MD, 21403

Lucy and Daniel are a great team for the best doggy daycare you could ever want/need for your dog! My dog is extremely needy and they gave him nothing but love. We look forward to next time!

Profile image
Meredith C.
Sitter Profile Image: Laura T.
Verified Enhanced Background Check
Laura T.
from
$40
per day
5.0 out of 5 stars
37 reviews
11 repeat clients
20 years of experience
Annapolis, MD, 21403

Laura is fantastic! Our pup Luna had a great time and loved playing around in the yard and with her two lovely pups. Laura was great to work with and sent pictures during Luna’s daycare session. Thanks!

Profile image
Mike H.
Sitter Profile Image: Julia H.
Verified Background Check
Julia H.
from
$85
per day
5.0 out of 5 stars
6 reviews
1 repeat client
30 years of experience
Annapolis, MD, 21403

Julia was incredibly responsive and promptly accepted our last-minute request. She took excellent care of our dog, providing frequent updates and photos that truly went above and beyond. She was attentive to his needs and very respectful of his comfort level. As a bonus, she has a delightful dog of her own, and ours clearly enjoyed the time playing together.

Profile image
Natalie K.
Sitter Profile Image: Lindsay M.
Verified Enhanced Background Check
Lindsay M.
Star Sitter
from
$55
per day
5.0 out of 5 stars
49 reviews
11 repeat clients
40 years of experience
Annapolis, MD, 21401

If I could give Lindsay 10 STARS I would!!! If you're traveling to the Annapolis area and don't know who to trust with your most precious asset - your pup (this was me!) - choose Lindsay! As you can see from all of Lindsays reviews, she is amazing with animals - its in her heart - but what makes Lindsay stands apart is her responsiveness, her communication, her ability to work with your schedule. She is so kind, and loving towards your dog, that you can enjoy your time away with peace in your heart. Thank you for everything Lindsay! <3

Profile image
Pamela C.
Sitter Profile Image: Andy & Lydia M.
Verified Enhanced Background Check
Andy & Lydia M.
Star Sitter
from
$55
per day
5.0 out of 5 stars
64 reviews
17 repeat clients
41 years of experience
Annapolis, MD, 21403

Andy & Lydia took wonderful care of our pup during his day visit in their home, he was so happy and energetic when we picked him up, we knew he had had a great time!

Profile image
Anna K.
Sitter Profile Image: Elaine S.
Verified Background Check
Elaine S.
from
$50
per day
5.0 out of 5 stars
69 reviews
37 repeat clients
20 years of experience
Annapolis, MD, 21403

Elaine takes such good care of our dog, Ellie. I'm so glad she was available to watch her when I had to be away for a work trip. I know she's in good hands! Thank you Elaine!

Profile image
Jessica A.
Sitter Profile Image: Lyndsy S.
Verified Enhanced Background Check
Lyndsy S.
from
$25
per day
5.0 out of 5 stars
30 reviews
10 repeat clients
30 years of experience
Annapolis, MD, 21403

About: I’m a full time teacher but am looking for something else to do with my weekends! I am also considering if I can make a living out of dog/cat/pet sitting. I work full time but have availability most evenings during the week and weekends to be able to do drop-ins and take care of your pet!! I would be able to sit for a cat or other pet who could be left at home all day any day of the week. I have a fenced in yard. I also live on a cul de sac which means there isn’t much car traffic…thus making my house a safe and calm place for your pet to stay!

Sitter Profile Image: Kacie B.
Verified Background Check
Kacie B.
Star Sitter
from
$45
per day
5.0 out of 5 stars
74 reviews
29 repeat clients
12 years of experience
Annapolis, MD, 21401

Had work done to my home and my puppy needed a place to stay for the day. Bruno had the best time with Kacie. I received so many updates and photos. It was so comforting to know he was in great hands.

Profile image
Katie F.
Sitter Profile Image: Taylor Grace T.
Verified Enhanced Background Check
Taylor Grace T.
from
$55
per day
5.0 out of 5 stars
8 reviews
1 repeat client
7 years of experience
Capitol Hill, Annapolis, MD, 21401

They were sweet with Kodi and sent picture updates during the day. I look forward to using them again!

Profile image
erin t.
Sitter Profile Image: Diana V.
Verified Enhanced Background Check
Diana V.
Star Sitter
from
$55
per day
5.0 out of 5 stars
206 reviews
90 repeat clients
10 years of experience
Riva, MD, 21140

Diana is awesome! She provides great communication throughout the stay and has a wonderful backyard for Remi to run around and play. Remi really enjoyed her stay.

Profile image
Deanna F.
Sitter Profile Image: Margriet M.
Verified Enhanced Background Check
Margriet M.
from
$75
per day
5.0 out of 5 stars
4 reviews
1 repeat client
17 years of experience
Annapolis, MD, 21403

About: I am a trustworthy, responsible, reliable, and caring person who loves dogs. To fill the void of not owning my own dog at the moment, I am available to help my friends and neighbors with their pets. I will treat your dog with love and genuine care. My schedule is quite flexible and includes weekend availability. I look forward to caring for your dog as if she/he were my own. Let’s connect. I am happy to make arrangements based on what is best and most comfortable for your dog. Let’s talk about what works for you and go from there.

Sitter Profile Image: Alex K.
Verified Enhanced Background Check
Alex K.
Star Sitter
from
$45
per day
5.0 out of 5 stars
62 reviews
15 repeat clients
30 years of experience
Annapolis, MD, 21401

Alex took care of Pepe like he was her own. I very much appreciate the videos, photos, and updates. She was very good at trying to bring Pepe out of his shell. I will book with Alex again!

Profile image
Louise J.
Sitter Profile Image: Liza S.
Verified Enhanced Background Check
Liza S.
Star Sitter
from
$65
per day
5.0 out of 5 stars
95 reviews
19 repeat clients
20 years of experience
Annapolis, MD, 21401

About: I'm a 32 y/o born & raised Annapolitan living in the heart of DT, and was raised always having 2 big dogs and 2 cats at a time. As of now, I travel to the Eastern Shore once a week to help my folks take care of our beloved Piper (13 y/o grandma Weimaraner) and Rooney (8 year old tabby). They are my world, but my heart is always open to giving all critters my love! Caring for and gaining the trust of an animal is truly one of life’s biggest rewards for me. I’m beyond grateful to be caring for the local dogs & cats of the area — thank you for your consideration! Dog Walking & Drop-In’s: These two services are very similar. You can customize either and both are the same fee. Let me know how you'd like me to spend my visit! (for example: out of a 30 minute visit — 15 minute walk, 15 minute outside play, etc.). The dog walking option does provide you with a map of our route. I'm happy to brush, feed, medicate your pets, water plants, grab the mail, clean the litter box or do simple tasks at no extra charge. I live 2 blocks away from my full time job downtown, which gives me a lot of flexibility. I’m sure to update my calendar regularly and only accept bookings that I know I can fully accommodate. My focus is on quality time, providing care and comfort crafted specifically for each animal, and respecting boundaries/safety. Let’s talk about what your pet prefers, and I’ll make it happen! 🫶

Sitter Profile Image: Whitney B.
Verified Enhanced Background Check
Whitney B.
from
$30
per day
5.0 out of 5 stars
60 reviews
21 repeat clients
14 years of experience
Annapolis, MD, 21401

Whitney is an excellent care provider for my fur baby! My girl suffers from separation anxiety and I needed someone she could hang out with when I was at work and my family was out of town. All I can say is this was the first time my baby was actually excited to leave me and stay with someone! She wagged her tail and easily went to Whittney when I dropped her off. Always came back to me happy and relaxed. Whittney was great sending me lots of pictures and she regularly took her for a walk. Plus, Whittney is so sweet herself, I want to be her friend!

Profile image
Kimberly H.
Sitter Profile Image: Alexis H.
Verified Enhanced Background Check
Alexis H.
from
$60
per day
5.0 out of 5 stars
5 reviews
13 years of experience
Annapolis, MD, 21403

About: I’ve been around animals my entire life and grew up caring for 3 dogs, 2 cats, birds, lizards, hermit crabs, fish, and rabbits. Taking care of pets has always come naturally to me. Since I was around 10 years old, I’ve helped walk my neighbors’ dogs and puppies, as well as pet sit their dogs and cats while they were away on vacation. I’m very patient, attentive, and love making pets feel safe, comfortable, and cared for like they’re part of the family. 🐾 Pet care fits naturally into my daily routine as a stay-at-home mom, which gives me a very flexible schedule and allows me to be home throughout the day for walks, feedings, playtime, check-ins, and lots of attention. My 5-month-old daughter and I spend a lot of time at home, so I’m able to provide consistent care, companionship, and updates for pet owners. I enjoy having animals as part of our daily routine and make sure every pet feels comfortable, safe, and cared for. In my home, pets are treated like family and are welcome on the furniture for comfort and companionship. I create a calm, loving environment where animals can feel safe and relaxed while away from their owners. My cats have access to food and water throughout the day, with their setup safely placed out of reach from dogs when needed. I do not crate animals unless specifically requested by the owner, as I prefer pets to feel comfortable and free in the home. I pay close attention to each pet’s routine, personality, and comfort level to make sure they receive individualized care, attention, and plenty of love.

Sitter Profile Image: Amy D.
Verified Enhanced Background Check
Amy D.
from
$45
per day
5.0 out of 5 stars
27 reviews
12 repeat clients
7 years of experience
Arnold, MD, 21012

Ed and Amy are pleasant and attentive to their pet guests. Plus, they are very good about making sure animals get bathroom breaks and exercise. In addition, Gunner’s warm demeanor always makes people feel welcome.

Profile image
Matthew H.
Sitter Profile Image: Michelle M.
Verified Background Check
Michelle M.
Star Sitter
from
$38
per day
5.0 out of 5 stars
556 reviews
257 repeat clients
25 years of experience
Annapolis, MD, 21409

I have used Michelle for both of my dogs, yesterday was her first time watching my 3 month old yorkie & she did a wonderful job. She made sure he was comfortable because he was afraid at first. I really appreciate Michelle for all of her help. I highly recommend her to anyone needing pet sitting services.

Profile image
Lor K.
Sitter Profile Image: Celena W.
Verified Enhanced Background Check
Celena W.
Star Sitter
from
$40
per day
5.0 out of 5 stars
11 reviews
3 repeat clients
4 years of experience
Annapolis, MD, 21409

Best experience I’ve had on rover! Maggie had a blast. Celena sent multiple updates throughout the day. This was a last minute booking and I’m so glad she was available, I will be booking with Celena again!

Profile image
Melissa S.
1 / 1
View more sitters

More than 1.6 million
pets enjoyed cuddles and care from sitters on Rover1

Adventure-ready dog walkers - Oakwood

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Lucille F.
Verified Enhanced Background Check
Lucille F.
from
$20
per walk
6 years of experience
Annapolis, MD, 21403

About: I've had numerous experiences caring for dogs of different temperaments and medical conditions, whether the animal was closely related through family or friends or through my place of work. Additionally, I am a former animal studies major and have spent several years learning and understanding different ways domesticated animals can communicate their needs. My goal is to ensure each animal is given the proper mental and physical enrichment they need to thrive in their loving home. Through my extensive research and knowledge, I foster a safe environment that ensures your dog/cat will receive the best care for their specific breed's needs and requirements. I strive every day to give each fur baby the love and life they deserve:) I have taken a few months away from my job to pursue personal passions of mine before I return to college, so my schedule from Monday to Sunday is very flexible and readily available. Times and schedules may vary depending on personal appointments or familial obligations. If for any reason an emergency visit is needed, I can swing by and check in with your fur baby. I can crate dogs easily and work on building confidence with shy/anxious dogs. Additionally, I update owners about patterns of feeding, bowel movements, or any changes in everyday life to ensure comfort. The safety of your pet is my top priority, and I strive to uphold that through attentive one-on-one play and monitoring of any physical or mental changes.

Sitter Profile Image: Ellie H.
Verified Enhanced Background Check
Ellie H.
from
$15
per walk
5.0 out of 5 stars
10 reviews
3 repeat clients
10 years of experience
Annapolis, MD, 21403

Ellie was great! She’s flexible and communicates well which makes it easy to trust her! She also did an outstanding job with my husky lab, Malibu. Would definitely recommend booking!

Profile image
Kaitlin N.
Sitter Profile Image: Mary H.
Verified Enhanced Background Check
Mary H.
from
$15
per walk
5.0 out of 5 stars
5 reviews
15 years of experience
Annapolis, MD, 21403

About: Hi! I’m Mary, but I usually go by Amber. I’ve raised and cared for dogs most of my life. I would love to help you with your check ins, walks, daycare, or boarding needs. I also have experience with medication administration if needed. I work part time, so I have a wide range of availability. I have a car and can drive to your location or host your loved one in my home. I have a single family house with a large fenced in yard. I also live in a big lovely neighborhood with plenty of space for walks. I do not currently have any pets, so your pet to have individual attention if required.

Sitter Profile Image: Elizabeth G.
Verified Enhanced Background Check
Elizabeth G.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
45 reviews
21 repeat clients
10 years of experience
Annapolis, MD, 21403

Thank you Elizabeth for taking great care of both dogs for us! We appreciate Elizabeth being patient as one of our dogs was hiding, afraid in a closet and she helped to get him out and comfortable on a walk.

Profile image
Brooke T.
Sitter Profile Image: Katherine V.
Verified Enhanced Background Check
Katherine V.
from
$15
per walk
15 years of experience
Annapolis, MD, 21403

About: Hi! I’m a dependable and caring pet lover who understands how important it is to feel confident leaving your pets in someone else’s care. I provide drop-in visits and dog walking services for both dogs and cats, and I treat every pet like part of the family. I have years of hands-on caregiving experience and am comfortable with pets of different ages, personalities, and energy levels — from playful puppies and active dogs to shy cats and senior pets who need a gentler approach. During drop-in visits and walks, I focus on giving pets attention, exercise, and consistency with their normal routine. I always provide updates and photos so owners can feel reassured their pets are doing well. Cats deserve just as much attention and care while their owners are away. I’m happy to provide: Feeding and water refresh Litter box cleaning Playtime and enrichment Medication assistance if needed Quiet companionship for shy cats Daily updates and photos

Sitter Profile Image: Megan T.
Verified Enhanced Background Check
Megan T.
from
$15
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
4 years of experience
Annapolis, MD, 21403

About: Hi! I'm a lifelong dog lover who grew up with 3 dogs, and regularly pet sit for friends and family before deciding to make it official. Friends often call me an animal whisperer because even shy or nervous pets tend to warm up to me quickly. I work remotely, and am very active, so I have a flexible schedule and can give your pet plenty of attention (and activity)! I work remotely and have very flexible hours, so your pet will have plenty of time, walking, snuggling, and being active. I also attend run clubs where pets are allowed, so if your fur baby is social, I’ll happily take them! I have a backyard, and live in a community with plenty areas to walk and sniff. Pets are welcome to be on furniture and in bed! I’m an excellent communicator, and will work collaboratively with you to determine the best care plan for your pet.

Sitter Profile Image: Laura D.
Verified Enhanced Background Check
Laura D.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
59 reviews
19 repeat clients
35 years of experience
Annapolis, MD, 21403

Laura was great! I made a mistake on the booking date, and she was kind enough to still go by and make sure my babies were taken care of despite my mistake. I will absolutely be working with her again. Highly recommend.

Profile image
Catie K.
Sitter Profile Image: Kathryn M.
Verified Enhanced Background Check
Kathryn M.
from
$20
per walk
11 years of experience
Annapolis, MD, 21403

About: I have had dogs for my entire life ranging from all ages! During my free time I am typically walking or taking care of my family’s American Bulldog, Axel. I also helped my college roommate raise and train her Pitbull. I am a recently graduated college student searching for work. In the meantime, I am dogsitting & walking while I search for a new career. Therefore, I have a very free & open schedule! I have a fenced yard in my home with a very friendly American Bulldog who would be happy to play with anyone! I am able to crate if needed.

Sitter Profile Image: Thomas R.
Verified Background Check
Thomas R.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
87 reviews
20 repeat clients
7 years of experience
Annapolis, MD, 21403

Thomas is so good working with our 14 1/2 year old black lab with some serious arthritis. He helps her up the stairs and competently gets her on and off the boat. When Thomas is here, we don’t worry about her while we are away. He goes above and beyond for our old girl with a smile and kind words.

Profile image
Dottie L.
Sitter Profile Image: Ally V.
Verified Enhanced Background Check
Ally V.
from
$20
per walk
4.5 out of 5 stars
3 reviews
1 repeat client
4 years of experience
Edgewater, MD, 21037

About: I have taken care of family and friends dogs most of my life. Love both dogs and cats! Always looking to make new furry friends I work from home so I am very flexible with my schedule and weekly routine. Reliable for last minute requests as well as long term ones Very flexible with different environments. I have a lot of experience with animals of different temperaments and always respect the owners wishes concerning how they would like their animals taken care of

Sitter Profile Image: Beth W.
Verified Enhanced Background Check
Beth W.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
72 reviews
32 repeat clients
25 years of experience
Annapolis, MD, 21403

Beth helped me out in a pinch and was great!

Profile image
Dana H.
Sitter Profile Image: Jessica B.
Verified Enhanced Background Check
Jessica B.
from
$25
per walk
5.0 out of 5 stars
9 reviews
5 repeat clients
12 years of experience
Edgewater, MD, 21037

Have had Jessica walk our dogs and also provide drop in visits while we were on vacation. She does a great job, lots of pics and our dogs love her. Would not hesitate to hire her again! Iggy and Obi love her.

Profile image
Hillary H.
Sitter Profile Image: Leigh Ann E.
Verified Enhanced Background Check
Leigh Ann E.
Star Sitter
from
$17
per walk
5.0 out of 5 stars
15 reviews
5 repeat clients
37 years of experience
Annapolis, MD, 21403

About: I’ve cared for dogs of all breeds & sizes over the years. I am comfortable with puppies through senior age. Friends, family and clients have relied on me to feed, walk, play with, clean up after, and love their pups as if they were my own. I can administer medications, including injections, and sq fluids. I can practice obedience skills during my visits as well. I’m available for pet care visits on Wednesday & Thursday mornings as well as evenings, Friday afternoon-evening, and all day on Saturdays and Sundays. I am also available on major holidays. Mondays and Tuesdays are on a case-by-case basis. I am very safety conscious and will care for your pets as carefully as I would my own. I will follow whatever your normal household routine is so that your pets feel safe and comfortable. They thrive with routines! If they use a crate, need treats after potty breaks, want belly rubs after a meal, etc., I am there for it all!

Sitter Profile Image: Elaine S.
Verified Background Check
Elaine S.
from
$20
per walk
5.0 out of 5 stars
69 reviews
37 repeat clients
20 years of experience
Annapolis, MD, 21403

About: I get a lot of pleasure assisting busy professionals with their pet sitting needs. I provide a nurturing and loving environment for your special pets in a very tranquil setting. Your pets will be treated as if they were my own. My husband and I will treat your pet with the utmost care and attention. References available upon request.

Sitter Profile Image: Harrison S.
Verified Enhanced Background Check
Harrison S.
from
$15
per walk
3 repeat clients
4 years of experience
Annapolis, MD, 21403

About: I’ve had dogs and cats my whole life growing up and been a pet owner for 18 years. I have walked, feed and cared for our family’s, friends, and neighbors. I’m am great with younger pets that need to release some energy and great with older pets that need a little bit more patience and time. I can’t wait to meet your pet and give a helping hand to your family. I’m completely flexible any days and times. Happy to do a meet and greet free of change! I currently own two pups named Dunkin and missy and a cat named bonnaroo. Which I care routinely. I don’t have any other big jobs right now so my main goal is focusing on the animals and making sure they get exercise. I love to get exercise and walk with my dogs. Also love to throw the ball with my dogs. By also Making sure they have food and water and stay healthy.

Sitter Profile Image: Ella L.
Verified Enhanced Background Check
Ella L.
from
$15
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
6 years of experience
Annapolis, MD, 21403

Ella has been an excellent dog walker for Cannon. She is extremely reliable and a great communicator. We would highly recommend her to care for your pets!

Profile image
Sadie S.
Sitter Profile Image: Stella N.
Verified Enhanced Background Check
Stella N.
from
$22
per walk
5.0 out of 5 stars
15 reviews
3 repeat clients
7 years of experience
Annapolis, MD, 21403

Stella is awesome with a great personality! She is timely and very reliable. We have 2 dogs and 1 puppy. She did an excellent job caring for them. She definitely loves animals. We felt so comfortable and had no worries leaving our fur babies with her.

Profile image
Charisse B.
Sitter Profile Image: Andrew P.
Verified Enhanced Background Check
Andrew P.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
66 reviews
19 repeat clients
15 years of experience
Annapolis, MD, 21403

Andrew did a great job this weekend! He walked my very large Labradoodle and St Bernadoodle and made sure both dogs and my 3 cats were fed and had water. He followed the care instructions, was extremely communicative and arrived promptly at the booking time. I will absolutely be using Andrew for future bookings, highly recommended!!

Profile image
Megan M.
Sitter Profile Image: Mark D.
Verified Enhanced Background Check
Mark D.
from
$20
per walk
5.0 out of 5 stars
3 reviews
2 repeat clients
30 years of experience
Annapolis, MD, 21403

Mark did a fantastic job with our new dog Teddy! We are long-time dog owners as is Mark, and his years of experience and bed-side manner was certainly evident and provided great peace of mind while we were away from our new pup. We will be relying on Mark in the future and strongly recommend him to others!

Profile image
Terry J.
Sitter Profile Image: Blinne F.
Verified Enhanced Background Check
Blinne F.
from
$18
per walk
5.0 out of 5 stars
20 reviews
6 repeat clients
20 years of experience
Annapolis, MD, 21403

Blinne was fabulous with my highly energetic pup and offered great feedback as to Kali’s behaviors after every walk. Kali would wait excitedly at the door each day for Blinne’s arrival. I will definitely reach out to Blinne again!

Profile image
Alison W.
1 / 1
View more sitters

Over 980,000
dogs traded couch time for play time with Doggy Day Care on Rover1

Large dog specialists near you - Oakwood

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Shelby B.
Verified Enhanced Background Check
Shelby B.
from
$57
per night
5.0 out of 5 stars
24 reviews
5 repeat clients
7 years of experience
Annapolis, MD, 21403

Moose had the best weekend with Shelby and her pup! It’s always nerve wracking when you leave your pet for the weekend but Shelby made us feel so comfortable by sending photos and treating Moose like her own. Highly recommend her to watch your fur baby!

Profile image
Samantha P.
Sitter Profile Image: Stacia D.
Verified Enhanced Background Check
Stacia D.
from
$60
per night
12 years of experience
Annapolis, MD, 21403

About: Hi there! My name is Stacia and I’ve taken care of animals my whole life. I am a dog owner too! Remi is a 2 years old, playful, dark yellow lab. He is fixed. I’m familiar with ensuring the environment is right for your dog. I previously owned a dog with high anxiety and wasn’t friendly with strangers. I understand the importance of making sure your guidelines for your pet are followed. I can give oral medications, follow your training rules, walk large dogs, handle dogs that aren’t friendly with strangers, high anxiety, and have disabilities (ex. Deaf, blind). These dogs are our best friends so I promise to take great care of yours :) If you have any additional questions for me, please don’t hesitate to ask. I am happy to chat or meet prior to booking to ensure I am a good fit for your pup! I believe in open communication to ensure the safety of you, your pet, me and mine. I work fully remote and am able to support daycare and boarding. I usually walk my dog morning, mid day and evening for 30 min to an hour at a time. I’d like to be able to support other people who need assistance. During the week your dog won’t be left alone for more than an hour depending on drop off and pick up time. During the weekend your dog won’t be left longer than 3-4 hours depending. We can always communicate your dogs specific needs to accommodate! I have a fenced yard in our home and a friendly, playful 2 year old male lab (fixed). If your dog is in my home, they do need to be friendly with other dogs. During the week I do work full time so there are times where I am in meetings so it is preferred your dog is not destructive or is okay in a crate or enclosed room during meetings. I do make sure the dogs are exercised before and after. I communicate my anticipated work schedule and plan for the day with the pet owner.

Sitter Profile Image: Carlie H.
Verified Enhanced Background Check
Carlie H.
Star Sitter
from
$45
per night
5.0 out of 5 stars
69 reviews
29 repeat clients
15 years of experience
Severna Park, MD, 21146

After a meet and greet we decided to do an overnight trial and our dog loved it! The whole family is very warm and inviting and our dog felt at home the moment he walked in the door. Their house has a nice fenced in backyard as a plus. We have already booked our summer vacation and plan on booking other trips as well. Very happy to have found such a perfect fit.

Profile image
Kathy T.
Sitter Profile Image: Megan T.
Verified Enhanced Background Check
Megan T.
from
$33
per night
5.0 out of 5 stars
5 reviews
1 repeat client
4 years of experience
Annapolis, MD, 21403

Meghan is easy to work with and super accommodating. Gave my girl, Aurora, lots of exercise and TLC. We loved our stay with her!

Profile image
Rob C.
Sitter Profile Image: James B.
Verified Enhanced Background Check
James B.
from
$40
per night
30 years of experience
Annapolis, MD, 21403

About: I've had dogs my whole life. Grew up in a house with 2+ dogs near constantly. All family dogs were 60+ lbs each with the largest being 110lbs. My 75lb dog crossed the rainbow bridge Sept 2025, I am not ready for a dog full time but I do miss the company. I will spoil your dog. I do not care about breed. I am looking for weekends. I work full time, so I am ready to go around noon on Friday and depending on the needs can be around all weekend. Generally I do leave the house during the weekend for a couple hours during the day to do chores and stuff but other than that can be a total home body. If the dog is good on leash I have a great neighborhood to take walks. If you are looking for me to stay at your house over the weekend, I can provide as much potty coverage as you request. If you want me to stay over the week, I do have a day job with my schedule being 7-3. I have a 8ft privacy fence the whole way around my backyard with a dog door. I do not have a crate, but I can use yours if you want your dog crated. I follow your food rules. I used to make hot breakfast/dinner for my dog. I do keep some dog treats in the house but I will check with you if your dog can have that specific treat first and if there are any dietary needs. If you want me to stay in your house, lets write the rules down and I'm happy to do whatever. If you have poor cellphone service, it'd be great to get a wifi password.

Sitter Profile Image: Thomas & Melissa S.
Verified Background Check
Thomas & Melissa S.
from
$60
per night
5.0 out of 5 stars
38 reviews
14 repeat clients
7 years of experience
Annapolis, MD, 21403

Trey and Melissa treated Abby like their own dog! They had great communication throughout the process and sent pictures and videos while we were away. We definitely recommended them!

Profile image
Kate D.
Sitter Profile Image: Tiffany C.
Verified Enhanced Background Check
Tiffany C.
from
$40
per night
5.0 out of 5 stars
5 reviews
1 repeat client
40 years of experience
Edgewater, MD, 21037

We thought we were having a good time until Tiffany sent pictures of our dogs. They were having the time of their lives! Tiffany is so kind and caring. She sent pictures of both dogs, cooked them food, let them sleep where they were comfortable. I couldn’t have picked a better person, and I will now only allow them to stay with Tiffany. Wonderful experience and big thanks to Tiffany!

Profile image
Stacy G.
Sitter Profile Image: Celena W.
Verified Enhanced Background Check
Celena W.
Star Sitter
from
$45
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
4 years of experience
Annapolis, MD, 21409

Celena was great! She sent tons pictures of our boy having a great time and she had plenty of updates. We also appreciate that she worked with us on our drop-off and pick-up times! We will definitely work with her again!

Profile image
Katie J.
Sitter Profile Image: Emily S.
Verified Enhanced Background Check
Emily S.
from
$60
per night
5.0 out of 5 stars
13 reviews
5 repeat clients
10 years of experience
Annapolis, MD, 21403

Emily was a fantastic sitter for Rudy! This was our first time with Emily and Rover and the experience was all positive. Emily kept in daily contact sending brief texts and/or pictures of Rudy that truly set my mind at ease during this first visit. Rudy also enjoyed playing with Emily's dogs, Pumpkin and Scooter. We would definitely use Emily again!

Profile image
Tracey B.
Sitter Profile Image: Anya B.
Verified Enhanced Background Check
Anya B.
from
$25
per night
8 years of experience
North Beach, Annapolis, MD, 21401

About: I have grown up with medium to large sized dogs my whole life. I have experience with very friendly dogs and dogs that cannot play with others as well as puppies to older dogs. I have cared for my own pets and friends while growing up and can be trusted with any task to ensure your pets needs and safety! I can offer dog walking in the mornings (7-9am) or afternoons (4-7pm) during the week or anytime during the weekends. I am available on the weekends to check-in or stay with your animal overnight as well. I can check-in and care for your animal during the day or overnight at clients homes. I will ensure your pet is fed, walked, bathed, played with and let outside for their needs. I am comfortable with any specific instructions from the owners as well (medication that needs to be taken, crate training, etc).

Sitter Profile Image: Lucy & Daniel M.
Verified Enhanced Background Check
Lucy & Daniel M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
17 reviews
4 repeat clients
15 years of experience
Annapolis, MD, 21403

Appreciate Lucy and Daniel so much, they did a wonderful job with our pup. Provided updates and were very communicative throughout booking and the stay, would absolutely trust them to watch our boy anytime.

Profile image
Hassie C.
Sitter Profile Image: Laura T.
Verified Enhanced Background Check
Laura T.
from
$60
per night
5.0 out of 5 stars
37 reviews
11 repeat clients
20 years of experience
Annapolis, MD, 21403

Belle’s time with Laura and Bunny was great!! My baby was full of life and energy! She definitely enjoyed her time, and I felt very comfortable that she was in good hands! The meet and greet was definitely the kick off to a wonderful stay! Thank you Laura and Bunny for taking such good care of Belle! See your gals soon!!

Profile image
Nicole D.
Sitter Profile Image: Candice W.
Verified Enhanced Background Check
Candice W.
Star Sitter
from
$65
per night
5.0 out of 5 stars
99 reviews
35 repeat clients
14 years of experience
Annapolis, MD, 21409

I would give 10 stars if I could! Phil was in excellent hands during his time with Candice & Rayne. She was very communicative with lots of pictures and updates, flexible and reliable with with a meet and greet, pick up and drop off. Phil had a great time and would love to come back and see Candice next time! Thank you!

Profile image
Olivia B.
Sitter Profile Image: Mady H.
Verified Enhanced Background Check
Mady H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
86 reviews
27 repeat clients
10 years of experience
Bowie, MD, 20716

This was our first time using Rover so we were nervous about leaving our fur baby with a Stanger in their home. Well Mady met and exceeded our expectations! We have a 96 pound Rottweiler and Mady loved on her and she enjoyed spending time with their dog Radar! She has a clean and spacious fenced in back yard and also took Stormy on nice walks! There were also toys there to keep Stormy occupied and happy. Mady followed our instructions exactly as it relates to her care. She sent pictures and videos which kept us from worrying! We highly recommend Mady, it’s clear this is not just a business for Mady, she truly has a love for dogs!

Profile image
Utokia L.
Sitter Profile Image: Riley N.
Verified Enhanced Background Check
Riley N.
from
$60
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
17 years of experience
Annapolis, MD, 21401

Riley was an outstanding sitter for our pup! He is a blind 10 yr old and she took the best care of him. She gave us updates throughout his stay and I really appreciated the pictures. If we’re ever in the area again, I would definitely trust Riley and she is our go to.

Profile image
Mackenzie G.
Sitter Profile Image: Sarah S.
Verified Enhanced Background Check
Sarah S.
from
$45
per night
5.0 out of 5 stars
15 reviews
3 repeat clients
20 years of experience
Annapolis, MD, 21401

Sarah made our dog Stuart feel perfectly at home with her family. She treated him like her own, and kept us in the loop with photo updates. We felt reassured and comforted knowing Stuart was in such loving hands. Thanks so much, Sarah!!

Profile image
Lauren R.
Sitter Profile Image: Lindsay G.
Verified Enhanced Background Check
Lindsay G.
Star Sitter
from
$49
per night
4.9 out of 5 stars
80 reviews
29 repeat clients
15 years of experience
Stevensville, MD, 21666

Lindsay, did a great job taking care of my dog and sent me pictures every day keeping me informed on how my dog was doing. I would highly recommend using Lindsay to take care of your dog. I was very pleased. Congressman Bill Sarpalius

Profile image
Bill S.
Sitter Profile Image: Kimberly W.
Verified Background Check
Kimberly W.
from
$45
per night
5.0 out of 5 stars
50 reviews
17 repeat clients
12 years of experience
Arnold, MD, 21012

Kimberly and her family took great care of our dog Winnie while we were away over the holiday break! She sent pictures every day of her enjoying time inside and outside on her walks about the neighborhood. We are so grateful that we found them and will definitely use her in the future! Thank you, Kimberly!

Profile image
Hayley M.
Sitter Profile Image: Andy & Lydia M.
Verified Enhanced Background Check
Andy & Lydia M.
Star Sitter
from
$65
per night
5.0 out of 5 stars
64 reviews
17 repeat clients
41 years of experience
Annapolis, MD, 21403

I really can't say enough great things about Andy & Lydia. They handled my dog so well, he had a super vacay away from the "parents". Lots of play time, snuggles, exercise, hanging out time, treats etc. I know he is dreaming about when he can go back and spend time with Andy, Lydia, and Luna. Andy was so considerate, patient, asked good questions about Rey's tendencies, health, etc. He even provided an Air Tag while Rey was in his care in case of an opportunistic escape to pursue something interesting. We received lots of great photos and very frequent updates which were wonderful. We are all looking forward to the next booking!

Profile image
Julie S.
Sitter Profile Image: Tyler G.
Verified Enhanced Background Check
Tyler G.
from
$30
per night
4.8 out of 5 stars
4 reviews
1 repeat client
1 year of experience
Shady Side, MD, 20764

Lovely couple with a baby and a toddler. Buffy had to warm up to Parker, their German Shepherd but I hear it went well. Tyler and wife watched Buffy on a holiday, July 4th. They were very gracious when I requested an itinerary change. I felt like they were really attuned to Buff-dog. Will definitely ask again for their assistance.Highly recommend.

Profile image
Penny B.
1 / 1
View more sitters

Not ready to book?

Get started building your pet's profile and discover trusted pet care in your neighborhood.

Pet care illustration

1Global data from Rover (November 2025)