Personalized care for your dog or cat - Sherwood Forest

Highly-rated overnight sitters - Sherwood Forest

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.
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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

Shuling is a wonderful sitter. She sent photos everyday and my dog looked very happy at her house. I'm so happy we can rely on Shuling to provide our pup with a safe, warm and relaxing place when we are out of town!

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Melinda S.
Sitter Profile Image: Carlie H.
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Carlie H.
Star Sitter
from
$45
per night
5.0 out of 5 stars
70 reviews
29 repeat clients
15 years of experience
Severna Park, MD, 21146

Carlie and her family are the best, they did an excellent job of looking after our Golden, giving him true home from home care. We would highly recommend.

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Anne Marie B.
Sitter Profile Image: Katelyn M.
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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

As always, Kate and her family are amazing! Buddy always has an awesome time and our minds are at ease knowing he’s in great hands while we’re away.

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Amy B.
Sitter Profile Image: Michelle M.
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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 was caring and really helpful on making our dogs feel at ease at her home. Sent us a bunch of pictures everyday and kept us informed on how the dogs were doing. I would definitely recomend her.

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Rita T.
Sitter Profile Image: Kimberly W.
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Kimberly W.
from
$45
per night
5.0 out of 5 stars
50 reviews
17 repeat clients
12 years of experience
Arnold, MD, 21012

Our pup was well taken care of, walks and ball chasing, lots of pictures showed the fun he was having. Kim even sent him home with a Christmas present- a stocking full of toys and treats.

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Cathy R.
Sitter Profile Image: Janice & Stalio C.
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Janice & Stalio C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
19 reviews
5 repeat clients
17 years of experience
Pasadena, MD, 21122

Our pets felt right at home with Janice and Stalio. They were so welcoming, helpful and accommodating with our boys. They kept us up to date daily with pictures and messages and even helped us out with making them their food because we miscounted the amount we sent. They provided amazing care and we look forward to rebooking with them in the future.

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Corisa W.
Sitter Profile Image: Jillian & Richard A.
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Jillian & Richard A.
Star Sitter
from
$49
per night
5.0 out of 5 stars
48 reviews
23 repeat clients
20 years of experience
Pasadena, MD, 21122

Jillian was the best! She treated our pet just as her own, and continuously provided us with heartwarming updates. We will definitely be using her in the future.

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Jillian F.
Sitter Profile Image: Katie F.
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Katie F.
from
$55
per night
5.0 out of 5 stars
115 reviews
36 repeat clients
16 years of experience
Annapolis, MD, 21401

Katie is amazing, can't recommend her enough. I can tell she's a true animal lover and Dirk ? was given great care. I would use her again in a heartbeat!

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Drew & Reid D.
Sitter Profile Image: Hester D.
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Hester D.
from
$35
per night
5.0 out of 5 stars
5 reviews
23 years of experience
Pasadena, MD, 21122

Hester was absolutely wonderful! Sent us updates on our boy while we were out of the country and shared about all the fun he was having. Would definitely rebook and recommend!!

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Megan C.
Sitter Profile Image: Candice W.
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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

Candice was great with our Bo. She sent loads of pictures (which we loved) and kept us up to date on feeding/sleeping schedules. We especially appreciated her flexibility on the pick up time. Thank you!!

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Sandy B.
Sitter Profile Image: Carla B.
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Carla B.
from
$45
per night
12 years of experience
Severna Park, MD, 21146

About: Dog mom to a friendly 3-year-old Lab mix and passionate about providing loving, attentive care. I’ve owned a dog for the past 12 years, but grew up caring for my friends and neighbors pets. Your pup will enjoy plenty of attention, walks on the Baltimore & Annapolis Trail, or relaxed time in our fenced backyard. Whether they’re young and energetic or a senior who prefers a slower pace, I’ll treat them like family and care for them as if they were my own. For boarding, during the work week we are not home from 8:30-2:30. We will be home all day on the weekends. For walking and drop ins, I am available in the afternoon and evening during the week, all day on the weekends. Your dog’s safety, comfort, and happiness are my top priorities. We have a secure fenced-in backyard where dogs can safely play, explore, and enjoy time outdoors. We have indoor cameras to monitor the house while we are at work. Our friendly 3-year-old Lab mix loves meeting new canine friends and provides great companionship for visiting dogs. I carefully supervise all interactions and make sure each dog feels comfortable in our home. We have an 11 year old and 6 year old that both grew up with a dog and are very caring and respectful of boundaries. They will be supervised while with your dog. Whether your pup enjoys active play, relaxing in the yard, or extra attention and cuddles, they’ll be treated like a member of the family in a safe, loving, and trustworthy environment.

Sitter Profile Image: Yukia G.
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Yukia G.
Star Sitter
from
$48
per night
5.0 out of 5 stars
64 reviews
15 repeat clients
20 years of experience
Crofton, MD, 21114

A very positive experience. My Bear received highly personalized care and a happy home to live & play in. Very communicative service and professional care! Highly recommended.

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Matthew M.
Sitter Profile Image: Celena W.
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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!

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Katie J.
Sitter Profile Image: Justine P.
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Justine P.
from
$55
per night
5.0 out of 5 stars
63 reviews
29 repeat clients
31 years of experience
Pasadena, MD, 21122

Justine was great. She has lots of experience, and a bunch of energetic playmate pups! I appreciated the quick drop-off/pick-up without a hassle. She’s quick to respond and sent pictures throughout the day.

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Jeremy D.
Sitter Profile Image: Nadia H.
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Nadia H.
from
$42
per night
5.0 out of 5 stars
55 reviews
25 repeat clients
6 years of experience
Odenton, MD, 21113

Nadia took great care of my dog while I was out of town! She gave me updates and shared videos and pictures throughout her stay. I look forward to using her again in the future for my dog sitting needs! 10/10!

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Jessica J.
Sitter Profile Image: Dana L.
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Dana L.
Star Sitter
from
$70
per night
5.0 out of 5 stars
35 reviews
13 repeat clients
20 years of experience
Arnold, MD, 21012

Dana is the perfect fit for our little nervous Annie. Dana respected my wishes and took extra time to make Annie comfortable. She even allowed our pup to sleep with her. I loved getting pictures and updates. We have been doing a few trial visits and now I have NO hesitation in using her for the week we go on vacation. Thank you Dana!

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Sheila S.
Sitter Profile Image: Becca K.
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Becca K.
Star Sitter
from
$60
per night
5.0 out of 5 stars
31 reviews
9 repeat clients
20 years of experience
Pasadena, MD, 21122

Becca did an awesome job watching Bodie while we were away. She was flexible, communicated well, and took great care of him. We really appreciated the updates and knowing he was in good hands. We’d definitely book with her again and highly recommend her to others.

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Corey P.
Sitter Profile Image: Peggy G.
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Peggy G.
Star Sitter
from
$42
per night
5.0 out of 5 stars
68 reviews
23 repeat clients
20 years of experience
Pasadena, MD, 21122

Peggy was very understanding and loving with Daisy. Daisy is a senior who at times requires a lot of attention. When I picked Daisy up she looked content. Usually when I board her it takes me a couple of days to settle her down. This was not the case with Peggy!

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Kathy W.
Sitter Profile Image: Shelby B.
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Shelby B.
from
$57
per night
5.0 out of 5 stars
24 reviews
5 repeat clients
7 years of experience
Annapolis, MD, 21403

Shelby was really great - she was flexible as my plans changed a bit and took Elmer to the park multiple times throughout his stay with her. He wasn’t anxious at all when I picked him up - always a sign he had a great weekend. Will definitely book with Shelby again!

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Gabby B.
Sitter Profile Image: ANGELA B.
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ANGELA B.
Star Sitter
from
$40
per night
5.0 out of 5 stars
18 reviews
4 repeat clients
20 years of experience
Odenton, MD, 21113

This was Tytus' first time away from us since his birth almost 5 years ago. Angela gave us a since of peace and comfort by providing us daily updates via text, photos, and videos. She and her daughter took great care of Tytus with giving him lots of love and hugs, which his very spoiled sweet spirit demands. I've already booked my next appointment and I would highly recommend her multiple services, which are flexible and reasonable. Thank you Angela for your exceptional service!

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Shirl C.
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Cat caregivers near you - Sherwood Forest

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

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

Heather was great. Super easy process, she came to the house for an initial meeting. She was very friendly and attentive. She sent me photos which I loved to receive while being gone. I will definitely use her on my next trip in September.

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Stephanie W.
Sitter Profile Image: Alexia M.
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Alexia M.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
39 reviews
14 repeat clients
10 years of experience
Annapolis, MD, 21409

Alexia is a Great Pet Sitter, she helped Rako out for 9 days, with our return He was Given Food and Water, and there was no mess. I love how she took care of his pads. Great Young Lady to hire.

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George G.
Sitter Profile Image: Jazmin G.
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Jazmin G.
from
$21
per visit
5.0 out of 5 stars
28 reviews
6 repeat clients
8 years of experience
21032

Jazmin is awesome!!! She treats our pets like they were her own. Highly recommend!

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Vicki S.
Sitter Profile Image: Allison K.
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Allison K.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
284 reviews
126 repeat clients
15 years of experience
Crownsville, MD, 21032

Allison took great care of our kitties while we were out of town. She really went the extra mile — coaxing our shy kitty out of hiding with his favorite treat and sweeping around the litter boxes. I always know my furry little guys are in great hands with Allison. 🐈‍⬛ 🐈

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Pamela W.
Sitter Profile Image: Marley D.
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Marley D.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
35 reviews
13 repeat clients
15 years of experience
Annapolis, MD, 21401

Marley was awesome. She did what she said she would do and took pictures and communicated with me during the day. Callie lover her too. Everyone should have a Marley. Will definitely call her again. TYVM Marley!

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Larry L.
Sitter Profile Image: Kayla G.
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Kayla G.
from
$18
per visit
5.0 out of 5 stars
31 reviews
11 repeat clients
15 years of experience
Arnold, MD, 21012

Kayla was an incredible sitter for my bunny! I have never felt more at peace when away from home. She always sent photos of Oliver as well as his food & water so that we knew he was all taken care of. I could tell that Oliver felt super comfortable with her which was amazing! We will definitely book with Kayla full time for any future dates.

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Ivy B.
Sitter Profile Image: Elizabeth "Phoenix" P.
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Elizabeth "Phoenix" P.
from
$18
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
20 years of experience
Annapolis, MD, 21401

Thanks Phoenix. Reliable, got the job done well and a caring person to trust with my cat visits. I appreciate you watching my kitty kid and will be in contact again for your great services ASAP.

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J C.
Sitter Profile Image: Bella N.
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Bella N.
from
$13
per visit
5.0 out of 5 stars
15 reviews
3 repeat clients
10 years of experience
Annapolis, MD, 21401

Bella did a great job! She was super easy to communicate with. Based on the pictures she sent of my cat, it seemed like Tabby really liked her, which is rare with pet sitters! I would definitely hire Bella again!

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Mary M.
Sitter Profile Image: Leigh Ann E.
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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

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Noah M.
Sitter Profile Image: Owen K.
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Owen K.
Star Sitter
from
$13
per visit
4.9 out of 5 stars
51 reviews
4 repeat clients
10 years of experience
Severna Park, MD, 21146

Owen was so kind, patient and helpful while we were away. He took care of everything that we asked and went above and beyond. Thank you so much! Definitely recommend working with him.

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Nina D.
Sitter Profile Image: Julia W.
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Julia W.
from
$23
per visit
5.0 out of 5 stars
9 reviews
1 repeat client
19 years of experience
Annapolis, MD, 21405

About: I’ve grown up with huskies and they are very high energy and active! I have experience with puppies as my sister adopted a chocolate lab puppy and I was over almost every week, including several different times where I watched him for a week on my own over the last year. I have also taken care of other small and large dogs and used to volunteer at Lucky Dog in D.C. where I walk ownerless dogs for free. My neighbor has relied on me to take care of her two cats for several different week-long occasions. I love playing with animals and will provide the best care because I know that our pets are our family. I work from home so I am able to watch pets during the day. I work from home Monday through Friday, so I am very flexible. I am able to let your pets out at any time of the day! I used to have a husky of my own so I know how important our “fur-babies” are to us. You can trust that I will give them the best belly rubs, treats, and take them on nice long walks. If you choose me as your pet caretaker you can guarantee your pet will get all the love and care they deserve!

Sitter Profile Image: Courtney A.
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Courtney A.
Star Sitter
from
$26
per visit
5.0 out of 5 stars
17 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!

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Anne-Katrin A.
Sitter Profile Image: Ava M.
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Ava M.
Star Sitter
from
$36
per visit
4.9 out of 5 stars
118 reviews
34 repeat clients
18 years of experience
Annapolis, MD, 21401

Ava is amazing! My family could no longer watch my two cats last minute before a long vacation, I had to find a cat sitter for the 1st time. Even though, I was a nervous Nelly, Ava totally put me at ease that my guys would be well taken care of. And they were!

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Shirey B.
Sitter Profile Image: Emma W.
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Emma W.
from
$18
per visit
5.0 out of 5 stars
100 reviews
46 repeat clients
13 years of experience
Pasadena, MD, 21122

Thank you Emma for your wonderful care!

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code g.
Sitter Profile Image: Anna M.
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Anna M.
from
$13
per visit
3 years of experience
Annapolis, MD, 21409

About: I’ve taken care of cats a few times throughout high school. I am able to spend time with your pets and work with their routine.

Sitter Profile Image: Leticia S.
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Leticia S.
from
$14
per visit
5.0 out of 5 stars
4 reviews
4 repeat clients
2 years of experience
Annapolis, MD, 21401

Leticia did a great job taking care of my cat Madison. Madison is a loner and doesn't warm up to people but he trusted Leticia from the start. I loved the photos and videos that she forwarded to me. It gave me peace of mind to know that he was well cared for. I hope that Leticia will be available the next time I need to be away from home for an extended period of time.

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Carolyn T.
Sitter Profile Image: Olivia S.
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Olivia S.
from
$32
per visit
5.0 out of 5 stars
36 reviews
11 repeat clients
13 years of experience
Annapolis, MD, 21401

Olivia did a wonderful job taking care of my cat, Cleopatra! She provided pictures and plenty of communication so I felt totally at ease while I was traveling. : )

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Jamie H.
Sitter Profile Image: Andrew P.
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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!!

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Alex P.
Sitter Profile Image: Mackenzie C.
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Mackenzie C.
from
$14
per visit
5.0 out of 5 stars
10 reviews
2 repeat clients
5 years of experience
Arnold, MD, 21012

Mackenzie was great! She connected with our cats so well and captured their personalities in daily update photos. Mackenzie is very responsive and reliable and we will be reaching out to her again. Thanks Mackenzie!!

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Lexie T.
Sitter Profile Image: Christopher Z.
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Christopher Z.
from
$17
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
3 years of experience
Arnold, MD, 21012

Great communication and everyone (cats and chickens!) was fed, clean, and happy!

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Allison S.
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Perfect for high energy dogs - Sherwood Forest

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

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Sitter Profile Image: Lindsay M.
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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

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Pamela C.
Sitter Profile Image: Danielle P.
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Danielle P.
from
$60
per day
5.0 out of 5 stars
20 reviews
5 repeat clients
20 years of experience
Arnold, MD, 21012

Danielle was the perfect sitter for my pups! She was incredibly easy to work with, responsive, and kind. My dogs absolutely loved their time with her. When I went to pick them up they didn’t want to leave! Would highly recommend. Thank you!!!

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Samantha F.
Sitter Profile Image: Kacie B.
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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.

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Katie F.
Sitter Profile Image: Alex K.
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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

First time my puppy was away from me and Alex kept me updated with lots of texts, pictures and videos. Winnie had a great time. Highly recommend.

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Christine H.
Sitter Profile Image: Amy D.
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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.

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Matthew H.
Sitter Profile Image: Dana L.
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Dana L.
Star Sitter
from
$60
per day
5.0 out of 5 stars
35 reviews
13 repeat clients
20 years of experience
Arnold, MD, 21012

Maggie had a great time having a calm day with Dana instead of staying home for our 3 year old daughter’s birthday party (with 12 other 3 year olds!) - Dana was really responsive and very responsible and Maggie was so happy!

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Virginia O.
Sitter Profile Image: Brittany K.
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Brittany K.
from
$40
per day
5.0 out of 5 stars
125 reviews
58 repeat clients
20 years of experience
Severna Park, MD, 21146

Brittany is the seriously best! She took care of my 2 year old labradoodle, and it was clear from the photos that my dog was having the time of her life in her big backyard and welcoming environment. Thank you, Brittany!

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Jill D.
Sitter Profile Image: Luba & James H.
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Luba & James H.
from
$40
per day
5.0 out of 5 stars
249 reviews
51 repeat clients
45 years of experience
Arnold, MD, 21012

Luba and James are great. They have a beautiful home with a nice fenced in backyard. Lilly received lots of love and had a lot of fun playing with their dog Nellie.

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Laura K.
Sitter Profile Image: Michelle M.
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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

Michelle took excellent care of my baby. We are getting used to a new area, and new people, and she made it that much easier for my Boston Terrier!

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Howard W.
Sitter Profile Image: Whitney B.
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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!

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Kimberly H.
Sitter Profile Image: Olga D.
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Olga D.
from
$50
per day
5.0 out of 5 stars
8 reviews
2 repeat clients
20 years of experience
Crownsville, MD, 21032

Very friendly and flexible. My dog was happy to stay with Olga. Thank you!

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Karen M.
Sitter Profile Image: Benjamin S.
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Benjamin S.
from
$27
per day
28 years of experience
Severna Park, MD, 21146

About: I am patient with dogs and am in tune with their behaviors, and will give them plenty of exercise if you'd like me to. Whether you need me to visit your dog's home or drop them off at mine, I'd be glad to help. I have a fenced in backyard with plenty of room to run and am a short distance from a bike trail that makes for good dog walking. I make it a point to take my own dog, Snickers on a walk at least once a day as well as playing fetch with her. I'd be happy to help keep your pet entertained as well I have a furbished basement that opens up to a fenced in backyard, with plenty of room for them to run around. Have toys to provide as well to keep them entertained. I just retired and am looking to help others with there pets and keep active.

Sitter Profile Image: Diana V.
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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

Let me just say Diana is awesome!!! She’s very responsive and took great care of our Ms Kenzie for 9 days . She provided updates and pictures throughout Kenzie’s stay and treated her like family. Our puppy decided to get in heat on day 2 or 3 but Diana handled it like the pro she is as we were concerned that it occurred while we were away. Diana had extra diapers and made sure she was comfortable. We were very appreciative of Diana’s attentiveness, love and care of our pooch and HIGHLY RECOMMEND Diana! Thank you so much Diana!!!!

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Shawn G.
Sitter Profile Image: Lucy & Daniel M.
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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!

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Meredith C.
Sitter Profile Image: Liza S.
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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: Celena W.
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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

Sooo easy to work with her under flexible conditions. My hound is a rescue from a nine-year life of abuse. Celena allowed Miguel and me to do a met and greet ahead of time so that it wouldn’t be a shock for him. He was treated as a visiting family member and enjoyed his stay.

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Patricia B.
Sitter Profile Image: Laura T.
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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!

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Mike H.
Sitter Profile Image: Ruth S.
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Ruth S.
from
$25
per day
5.0 out of 5 stars
23 reviews
8 repeat clients
40 years of experience
Millersville, MD, 21108

Ruth provided excellent service and was flexible in meeting my schedule. She is very friendly and quickly responded to my text messages with all questions answered. She shared her awesome home with Loki for the day and he thoroughly enjoyed himeself. I will definately contact her for the next time I need a pup sitter. Thanks Ruth.

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Robert W.
Sitter Profile Image: Janice & Stalio C.
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Janice & Stalio C.
Star Sitter
from
$50
per day
5.0 out of 5 stars
19 reviews
5 repeat clients
17 years of experience
Pasadena, MD, 21122

Wonderful people! Great with our dog!!

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Cindy H.
Sitter Profile Image: Naya M.
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Naya M.
Star Sitter
from
$45
per day
5.0 out of 5 stars
90 reviews
29 repeat clients
25 years of experience
Millersville, MD, 21108

Naya is AMAZING! My husband and I have a long commute and needed someone to take care of our pup during the way while we're at work. Before we found Naya, we were really concerned about leaving him somewhere else for so long during the day. But we really lucked out in finding Naya! Naya has her own 2 dogs and a huge backyard that our pup loves to play in! She takes him for walks, teaches him tricks, and helps us so much by training with him as well! Our pup comes home every day happy and tired, and is excited to go back in the morning. Naya is so attentive, caring, and loving to our pup and we feel so lucky that we found her!

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Mikala H.
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Adventure-ready dog walkers - Sherwood Forest

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

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Sitter Profile Image: Marley D.
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Marley D.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
35 reviews
13 repeat clients
15 years of experience
Annapolis, MD, 21401

Marley has been an awesome dog walker for our dog twice a week. She takes very good care of him and has been great with communication. Would highly recommend Marley!

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Brad F.
Sitter Profile Image: Owen K.
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Owen K.
Star Sitter
from
$15
per walk
4.9 out of 5 stars
51 reviews
4 repeat clients
10 years of experience
Severna Park, MD, 21146

Owen is reliable, kind and trustworthy. He shows up, gives my dog a good walk regardless of the weather, and responds quickly. I highly recommend him to anyone that needs a walker.

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James T.
Sitter Profile Image: Nolan C.
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Nolan C.
from
$15
per walk
10 years of experience
Annapolis, MD, 21409

About: I have taken care of different types of dogs and including in home stay, walks, puppies etc and had my own dog since I was 12. I have lots of experience in caring for animals from reptiles to mammals. I am very physically active and love to spend time outside so long walks and exercise is both fun for me and your pet. I am currently looking for a part time job my schedule is open for the relative future and any changes to my schedule will be minimal, I am fully available for a consistent walking or care schedule for your pet. I care for my dog with long walks, exercise/play time with his favorite toys or enrichment games. I also have a back and front yard at my house that my dog loves to play in with a park and beach access that allows dogs. When I care for bigger dogs I love to take them to the park in my neighborhood or one nearby to play fetch.

Sitter Profile Image: Sylvie L.
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Sylvie L.
from
$17
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
22 years of experience
Annapolis, MD, 21401

About: I love animals so much(perhaps more than people...). I have experience in taking care of dogs of various sizes and temperaments. Growing up I've had a puggle, boxer, and now two german shepherd mixes who were adopted from shelters. I've volunteered at animal shelters where I walked, cleaned, brushed, and fed dogs. Furthermore, I've pet sat for neighbors and family members. My dogs live with my parents in Cascade, so I don't live with dogs nor other humans at my house in Annapolis. I would love to take care of your pets! I will be starting a program that runs from M-F 9-3:30 soon, but am available after 3:30 M-F and all day on Saturdays/Sundays. I could walk, feed, or let out your pets before 9 as well. The M-F schedule will change come the end of July which would give me more availability on those days. When I'm at my parent's house, I let my dogs out in the mornings, feed them breakfast and dinner, give them medicine, go on walks/hikes, practice tricks and obedience tasks with them, and play with them. I'm more than happy to provide these services in my client's home too!

Sitter Profile Image: Alexia M.
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Alexia M.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
39 reviews
14 repeat clients
10 years of experience
Annapolis, MD, 21409

We absolutely love, Alexia! She is consistently punctual and genuinely engages with our dog during his walks. What really stands out as how well she manages him, especially when he gets reactive around cars and certain dogs. Alexia took the time to do a meet and greet before our first walk, which made all the difference in ensuring everything went smoothly. We've already booked her for multiple walks and will definitely continue using her services. We feel so fortunate to have found her!

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Nathaniel V.
Sitter Profile Image: Kathryn U.
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Kathryn U.
from
$18
per walk
5.0 out of 5 stars
19 reviews
4 repeat clients
10 years of experience
Annapolis, MD, 21401

About: I’ve had experience with small and medium size dogs for several years and also have two of my own at home so I understand how important it is to know they are well cared for. I promise to love and take care of them while their parents are away. I work hybrid so I have plenty of time to make sure your pets are cared for and walked every 2-4 hours and kept on their normal schedule. I will take good care of them and also protect your home and keep it clean. Pets will feel comfortable and safe in their home environment.

Sitter Profile Image: Anna M.
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Anna M.
from
$15
per walk
6 years of experience
Annapolis, MD, 21409

About: I’ve taken care of dogs and cats since I was in high school. I am patient attentive, and have a flexible schedule to take care of your pets. I work part time and mostly at night so I will be able to spend a lot of time during the day with your pets. I can easily get to a clients home and am able to stay there with them as needed. I can spend plenty of time with your pets and give them plenty of attention.

Sitter Profile Image: Julia W.
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Julia W.
from
$25
per walk
5.0 out of 5 stars
9 reviews
1 repeat client
19 years of experience
Annapolis, MD, 21405

About: I’ve grown up with huskies and they are very high energy and active! I have experience with puppies as my sister adopted a chocolate lab puppy and I was over almost every week, including several different times where I watched him for a week on my own over the last year. I have also taken care of other small and large dogs and used to volunteer at Lucky Dog in D.C. where I walk ownerless dogs for free. My neighbor has relied on me to take care of her two cats for several different week-long occasions. I love playing with animals and will provide the best care because I know that our pets are our family. I work from home so I am able to watch pets during the day. I work from home Monday through Friday, so I am very flexible. I am able to let your pets out at any time of the day! I used to have a husky of my own so I know how important our “fur-babies” are to us. You can trust that I will give them the best belly rubs, treats, and take them on nice long walks. If you choose me as your pet caretaker you can guarantee your pet will get all the love and care they deserve!

Sitter Profile Image: Allison K.
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Allison K.
Star Sitter
from
$21
per walk
4.9 out of 5 stars
284 reviews
126 repeat clients
15 years of experience
Crownsville, MD, 21032

We've only been working with Allison for a short while but she's been so great. She's very communicative, responsive, and our pup definitely seems we'll taken care of. We feel like we don't have to worry about her while we're out and about. All the stars!!

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Heather R.
Sitter Profile Image: Jacob B.
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Jacob B.
from
$30
per walk
5.0 out of 5 stars
91 reviews
18 repeat clients
15 years of experience
Crownsville, MD, 21032

Jacob was very responsive and he was great with my pups. He was flexible with the schedule to accommodate the needs of my pups. He was very friendly and the pups seems to look forward to seeing him. We will definitely use him again.

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Erin L.
Sitter Profile Image: Courtney A.
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Courtney A.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
17 reviews
4 repeat clients
15 years of experience
Parole, MD

About: Hi! I’m Courtney — a true dog lover, experienced pet caregiver, and someone who treats every pet like family. As a dog mom myself, I understand how important it is to trust the person caring for your pet. Whether your dog loves long walks, playtime, couch snuggles, or just a calm and reassuring presence, my goal is to make them feel safe, comfortable, and loved while you’re away. I have extensive experience caring for dogs with a wide range of personalities, energy levels, and care needs, and I pride myself on being dependable, communicative, and attentive to details. For house sitting, my standard rate includes typical care such as feeding, walks/potty breaks, companionship, overnight care, and lots of love. If your pet requires additional support — including senior care, medication administration, frequent potty breaks (every few hours), mobility assistance, separation anxiety management, or near-constant supervision — please let me know before booking, as these higher-needs situations may require custom pricing to ensure I can provide the level of care your pet deserves. Please be as detailed as possible about your pet’s routine, behaviors, and care needs so I can make sure we’re the right fit. Looking forward to meeting your furry family member!

Sitter Profile Image: Kayla G.
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Kayla G.
from
$20
per walk
5.0 out of 5 stars
31 reviews
11 repeat clients
15 years of experience
Arnold, MD, 21012

Kayla was fantastic with our dog, Kona! She communicated clearly, sent great photo updates, and was very respectful of our home. Kona loved her walks and came back happy every time. Highly recommend!

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Nicole M.
Sitter Profile Image: Mackenzie C.
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Mackenzie C.
from
$15
per walk
5.0 out of 5 stars
10 reviews
2 repeat clients
19 years of experience
Arnold, MD, 21012

MacKenzie has been great with walking my very energetic (and demanding) Yorkie. She is professional, polite, prompt. Any complaints? Psssh, nope. Thank you MacKenzie!!

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April J.
Sitter Profile Image: Tiffany O.
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Tiffany O.
from
$20
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
30 years of experience
Annapolis, MD, 21409

About: I am a true animal lover. I think animals become our family and I want you to feel comfortable that I will treat your pet like my own went in my care. I have experience with many kinds of animals, dogs, cats, hamsters, and reptiles. I am patient and kind and love to get to know your pet. This is currently my only job, so my schedule is very flexible. I am available morning, afternoons and evenings for visits. I can help on weekdays or weekends. I first get to know your pets basic needs, ensuring their safety, and offering enrichment. This includes feeding, providing fresh water, ensuring proper elimination, creating a safe and comfortable environment, offering exercise and playtime, and attending to any medical or behavioral needs. I am comfortable with small and large dogs as well as small pets and reptiles.

Sitter Profile Image: Samantha C.
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Samantha C.
from
$18
per walk
5.0 out of 5 stars
25 reviews
8 repeat clients
6 years of experience
Annapolis, MD, 21401

Samantha was great with DaVinci

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Chris A.
Sitter Profile Image: Heather B.
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Heather B.
Star Sitter
from
$28
per walk
5.0 out of 5 stars
158 reviews
51 repeat clients
17 years of experience
Annapolis, MD, 21401

Heather was fantastic, responsible, punctual, and clearly great with dogs. Chance warmed up to her right away, and I appreciated the updates and photos. I will definitely book her again.

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Sitter Profile Image: Chelsea F.
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Chelsea F.
from
$25
per walk
20 years of experience
Annapolis, MD, 21401

About: I’ve grown up with pets ranging from beta fish, dogs, guinea pigs and gerbils! I’ve watched my friend’s pets over the years as well. My cat who unfortunately passed had kidney issues so I have experience in dealing with that. I’m also a volunteer with the SPCA! I’m currently working a full time job, but work locally and have a hybrid schedule so I can be fairly flexible in the evenings and weekends! I could also be available around lunchtime during the week. My cat who unfortunately has now passed pretty much owned the second bedroom and bathroom in my home. I always made sure she is comfy, happy and had lots of boxes and her favorite string (she refused to use an actual cat bed but LOVES boxes!) I will make sure your pet is always well cared for, loved (if they desire) and catered to whatever they need (even if it’s a box)!

Sitter Profile Image: Riley H.
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Riley H.
from
$20
per walk
1 year of experience
Severna Park, MD, 21146

About: I love dogs and have nothing else to do and your dog will be my entire focus. I have had 3 dogs since I was a kid and have baby sat them and my sister’s dog. I am around the whole summer and would love to watch your dogs. I have also helped train my dogs and gone to training for them as well. I have watched my 2 digs for over a week on my own and my sisters for a week as well I will shape my day around your dog and any dogs I am sitting or watching that day. I have nothing this summer. The only activity I do regularly is lift. If your dog needs a morning walk I will lift later same goes for afternoon walks If you have a fenced yard I will play with your dog after the walk and make sure they get lots of treats and attention

Sitter Profile Image: Bella N.
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Bella N.
from
$16
per walk
5.0 out of 5 stars
15 reviews
3 repeat clients
10 years of experience
Annapolis, MD, 21401

Bella was very accommodating with both of our dogs, Miko and Ren. Would definitely recommend and rebook!

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Luke G.
Sitter Profile Image: Jazmin G.
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Jazmin G.
from
$23
per walk
5.0 out of 5 stars
28 reviews
6 repeat clients
9 years of experience
Crownsville, MD, 21032

Jazmin was great with all 3 doggies. Fed them as well!

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Spencer H.
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Large dog specialists near you - Sherwood Forest

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

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

Carlie and her family are the best, they did an excellent job of looking after our Golden, giving him true home from home care. We would highly recommend.

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Anne Marie B.
Sitter Profile Image: Kimberly W.
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Kimberly W.
from
$45
per night
5.0 out of 5 stars
50 reviews
17 repeat clients
12 years of experience
Arnold, MD, 21012

Our pup was well taken care of, walks and ball chasing, lots of pictures showed the fun he was having. Kim even sent him home with a Christmas present- a stocking full of toys and treats.

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Cathy R.
Sitter Profile Image: Jillian & Richard A.
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Jillian & Richard A.
Star Sitter
from
$49
per night
5.0 out of 5 stars
48 reviews
23 repeat clients
20 years of experience
Pasadena, MD, 21122

Jillian was the best! She treated our pet just as her own, and continuously provided us with heartwarming updates. We will definitely be using her in the future.

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Jillian F.
Sitter Profile Image: Hester D.
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Hester D.
from
$35
per night
5.0 out of 5 stars
5 reviews
23 years of experience
Pasadena, MD, 21122

Hester was absolutely wonderful! Sent us updates on our boy while we were out of the country and shared about all the fun he was having. Would definitely rebook and recommend!!

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Megan C.
Sitter Profile Image: Candice W.
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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

Candice was great with our Bo. She sent loads of pictures (which we loved) and kept us up to date on feeding/sleeping schedules. We especially appreciated her flexibility on the pick up time. Thank you!!

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Sandy B.
Sitter Profile Image: Carla B.
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Carla B.
from
$45
per night
12 years of experience
Severna Park, MD, 21146

About: Dog mom to a friendly 3-year-old Lab mix and passionate about providing loving, attentive care. I’ve owned a dog for the past 12 years, but grew up caring for my friends and neighbors pets. Your pup will enjoy plenty of attention, walks on the Baltimore & Annapolis Trail, or relaxed time in our fenced backyard. Whether they’re young and energetic or a senior who prefers a slower pace, I’ll treat them like family and care for them as if they were my own. For boarding, during the work week we are not home from 8:30-2:30. We will be home all day on the weekends. For walking and drop ins, I am available in the afternoon and evening during the week, all day on the weekends. Your dog’s safety, comfort, and happiness are my top priorities. We have a secure fenced-in backyard where dogs can safely play, explore, and enjoy time outdoors. We have indoor cameras to monitor the house while we are at work. Our friendly 3-year-old Lab mix loves meeting new canine friends and provides great companionship for visiting dogs. I carefully supervise all interactions and make sure each dog feels comfortable in our home. We have an 11 year old and 6 year old that both grew up with a dog and are very caring and respectful of boundaries. They will be supervised while with your dog. Whether your pup enjoys active play, relaxing in the yard, or extra attention and cuddles, they’ll be treated like a member of the family in a safe, loving, and trustworthy environment.

Sitter Profile Image: Yukia G.
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Yukia G.
Star Sitter
from
$48
per night
5.0 out of 5 stars
64 reviews
15 repeat clients
20 years of experience
Crofton, MD, 21114

A very positive experience. My Bear received highly personalized care and a happy home to live & play in. Very communicative service and professional care! Highly recommended.

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Matthew M.
Sitter Profile Image: Celena W.
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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!

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Katie J.
Sitter Profile Image: Justine P.
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Justine P.
from
$55
per night
5.0 out of 5 stars
63 reviews
29 repeat clients
31 years of experience
Pasadena, MD, 21122

Justine was great. She has lots of experience, and a bunch of energetic playmate pups! I appreciated the quick drop-off/pick-up without a hassle. She’s quick to respond and sent pictures throughout the day.

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Jeremy D.
Sitter Profile Image: Dana L.
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Dana L.
Star Sitter
from
$70
per night
5.0 out of 5 stars
35 reviews
13 repeat clients
20 years of experience
Arnold, MD, 21012

Dana is the perfect fit for our little nervous Annie. Dana respected my wishes and took extra time to make Annie comfortable. She even allowed our pup to sleep with her. I loved getting pictures and updates. We have been doing a few trial visits and now I have NO hesitation in using her for the week we go on vacation. Thank you Dana!

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Sheila S.
Sitter Profile Image: Becca K.
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Becca K.
Star Sitter
from
$60
per night
5.0 out of 5 stars
31 reviews
9 repeat clients
20 years of experience
Pasadena, MD, 21122

Becca did an awesome job watching Bodie while we were away. She was flexible, communicated well, and took great care of him. We really appreciated the updates and knowing he was in good hands. We’d definitely book with her again and highly recommend her to others.

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Corey P.
Sitter Profile Image: Peggy G.
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Peggy G.
Star Sitter
from
$42
per night
5.0 out of 5 stars
68 reviews
23 repeat clients
20 years of experience
Pasadena, MD, 21122

Peggy was very understanding and loving with Daisy. Daisy is a senior who at times requires a lot of attention. When I picked Daisy up she looked content. Usually when I board her it takes me a couple of days to settle her down. This was not the case with Peggy!

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Kathy W.
Sitter Profile Image: Shelby B.
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Shelby B.
from
$57
per night
5.0 out of 5 stars
24 reviews
5 repeat clients
7 years of experience
Annapolis, MD, 21403

Shelby was really great - she was flexible as my plans changed a bit and took Elmer to the park multiple times throughout his stay with her. He wasn’t anxious at all when I picked him up - always a sign he had a great weekend. Will definitely book with Shelby again!

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Gabby B.
Sitter Profile Image: Brittany K.
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Brittany K.
from
$40
per night
5.0 out of 5 stars
125 reviews
58 repeat clients
20 years of experience
Severna Park, MD, 21146

Brittany took great care of my Old English Sheepdog! She responded quickly and sent multiple pictures a day since she knew I was missing my girl. I felt at ease knowing that my dog was in great hands and was truly part of Brittany's family while I was away. I even found out that my dog had a favorite spot on her couch. I highly recommend Brittany and would use her again in a heartbeat!

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Anna T.
Sitter Profile Image: Kendall L.
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Kendall L.
from
$50
per night
5.0 out of 5 stars
6 reviews
1 repeat client
18 years of experience
Severna park, MD, 21146

Kendall was great with my puppy! She wore my dog out with lots of playtime and care and was very communicative. I'll absolutely book with Kendall again!

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Ashley T.
Sitter Profile Image: Mady H.
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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

Lexi absolutely LOVES spending time with Mady and her family. Mady is great and I truly feel like Lexi is home at Mady’s home. Mady sends updates with pics to let us know how Lexi is doing. We are keeping Mady on speed dial?

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Melina S.
Sitter Profile Image: Luba & James H.
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Luba & James H.
from
$50
per night
5.0 out of 5 stars
249 reviews
51 repeat clients
45 years of experience
Arnold, MD, 21012

Luba and James are wonderful. Oliver always comes home exhausted and happy from walks and playing with Nellie. Thanks for taking such good care of him!

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Laurie M.
Sitter Profile Image: Tanya M.
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Tanya M.
from
$45
per night
5.0 out of 5 stars
29 reviews
8 repeat clients
7 years of experience
Glen Burnie, MD, 21061

I had a wonderful experience with Tanya while she cared for my 14 year old yorkie, Buttons. She was extremely attentive to Buttons and his individual needs, and it was clear she was committed to helping him feel comfortable and acclimated to a new environment. She kept me informed every four hours or so with updates, which truly gave me peace of mind and made me feel completely comfortable leaving Buttons in her care. I’m so grateful for the care and attention she provided, and I wouldn’t hesitate to book with her again.

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Sherreka J.
Sitter Profile Image: Elena K.
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Elena K.
Star Sitter
from
$40
per night
5.0 out of 5 stars
14 reviews
2 repeat clients
10 years of experience
Annapolis, MD, 21409

Elena did an amazing job with our Old English Sheepdog Lady. I could really tell that she loves taking care of animals, and she did a great job. Our dog was pretty nervous as she went to the vet the day before, but Eleana made her feel at home and I thank her for that. I highly recommend her.

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Daniel B.
Sitter Profile Image: Anya B.
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Anya B.
from
$25
per night
5.0 out of 5 stars
4 reviews
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).

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