Personalized care for your dog or cat - Rolling Hills

Highly-rated overnight sitters - Rolling Hills

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: Shuling J.
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Shuling J.
Star Sitter
from
$45
per night
5.0 out of 5 stars
152 reviews
69 repeat clients
8 years of experience
Annapolis, MD, 21401

Shuling did a nice job of taking caring for our 9lb guy, Scout. He is now 14+ years old and she did a great job of taking care of his needs. Thanks Shuling! Sean

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

Another stay with Carlie and we cannot recommend her enough! We always have such peace of mind with her daily updates and photos and knowing that our pup, Indi, is safe and having fun. Indi gets her own vacation when she stays here and we love knowing that our she gets to enjoy herself, too! Between Carlie's loving and kind family, the huge bonus yard, and Carlie's attention and ability to continue medicine (she even notices any behavioral changes!), we just know we've made the right choice. Do yourself a favor, and get on her schedule for your pup sitting needs! :)

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Kyanna 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
25 repeat clients
8 years of experience
Arnold, MD, 21012

Katelyn provided the most amazing care for our puppy!! He was spoiled with multiple walks, many treats, and tons of snuggles while we were away for a long weekend. He became friends with their sweet husky as well. Can’t wait for him to stay with her family again soon!! Thank you!!

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Morgan S.
Sitter Profile Image: Michelle M.
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Michelle M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
557 reviews
258 repeat clients
25 years of experience
Annapolis, MD, 21409

I highly recomend Michele. She was always quick to respnd. She sent many pictures every day so I could see that my boy was enjoying his stay. She has a beautiful backyard that my boy enjoyed running around. The best part of my boys stay at Michele's house is that he made a bunch of new playmates cand canine fcompanions.

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Dean B.
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!!! Cooper absolutely loved her and she took such great care of him! And took great care of us dog parents - sending such thoughtful picture and video updates !

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Holly S.
Sitter Profile Image: Diana V.
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Diana V.
Star Sitter
from
$57
per night
5.0 out of 5 stars
213 reviews
93 repeat clients
10 years of experience
Riva, MD, 21140

Moose absolutely loved his vacation with Diana. I’d never left him with anyone before and she made me feel completely comfortable. I’ll definitely be a repeat client ?

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Kristin T.
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

Yukia did a fantastic job with our dog, Sammy! Communication regarding pickup and drop off was excellent and we got some pictures of Sammy on a regular basis. Would definitely book with Yukia again!

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Stephen G.
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

This was Balee's first boarding stay with Mady. She and her family were Ah-Mazing! I felt bad leaving because of an ear infection that he was diagnosed with a day before our departure. Balee received lots of TLC during his visit and Mady kept me updated about his adjustment daily (which was comforting).

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Temeka P.
Sitter Profile Image: Kimberly W.
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Kimberly W.
from
$45
per night
5.0 out of 5 stars
51 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!

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Hayley M.
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
6 repeat clients
17 years of experience
Pasadena, MD, 21122

If I could give more than five stars, I would! Janice and Stalio were wonderful dog sitters to my two toy fox terriers. They sent updates and photos during my trip to Iceland for a week. No complaints whatsoever, I couldn’t recommend them more!

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Chelsea G.
Sitter Profile Image: ANGELA B.
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ANGELA B.
Star Sitter
from
$40
per night
5.0 out of 5 stars
19 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.
Sitter Profile Image: Nadia H.
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Nadia H.
from
$42
per night
5.0 out of 5 stars
55 reviews
26 repeat clients
6 years of experience
Odenton, MD, 21113

During my elderly dog’s 17 days of stay, Nadia provided frequent updates and pictures and communicated with me regularly. My dog looked really well when we picked her up. I was very nervous since she never stayed w a dog-sitter before. I am very grateful. Thank you, Nadia.

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Ozlem B.
Sitter Profile Image: Hester D.
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Hester D.
from
$38
per night
5.0 out of 5 stars
6 reviews
1 repeat client
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: Brittany I.
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Brittany I.
Star Sitter
from
$42
per night
5.0 out of 5 stars
27 reviews
7 repeat clients
15 years of experience
Gambrills, MD, 21054

Fabulous! Thank you! Chester (our adrenaline junkie border collie) is tired and had a great time with Gryph! Nice big backyard - easy to park and drop off. We’ll be back!

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Juliana A.
Sitter Profile Image: Gurbata Michelle A.
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Gurbata Michelle A.
from
$30
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
20 years of experience
Odenton, MD, 21113

Ahhhmazing!!! Michelle will absolutely be our go to dog sitter! Oliver is still a puppy so he is high energy and still working on his potty training. This was our first time using rover and his first time away from us. Michelle took care of him above and beyond our expectations! She sent us model pictures of him daily (much better than he lets us take of him, so we have new profile pics of him, lol!) She provided daily updates with the pics too, all of which gave us complete peace of mind! We couldn’t have had a better experience and that made our vacation that much more relaxing. We are extremely thankful to Michelle for treating Oliver like her own! 😊

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Destanie S.
Sitter Profile Image: Elena K.
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Elena K.
Star Sitter
from
$40
per night
5.0 out of 5 stars
17 reviews
3 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: Candice W.
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Candice W.
Star Sitter
from
$65
per night
5.0 out of 5 stars
100 reviews
35 repeat clients
14 years of experience
Annapolis, MD, 21409

We highly recommend Candice! She will love your pup as her own! She took great care of our pup and sent lots of photos. She has a big yard and room for the pups as well! Our dog also has a bit of energy so it was perfect that he could play with her pup as well. He came home worn out and well loved!!

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Matt & Taylor T.
Sitter Profile Image: Carla B.
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Carla B.
from
$40
per night
5.0 out of 5 stars
5 reviews
12 years of experience
Severna Park, MD, 21146

We had a wonderful experience boarding our pup in Carla's home! Our dog was so well cared for, and Carla sent daily updates with pictures and videos. Her dog was incredibly sweet and got along great with ours. She did a great job balancing exercise with being mindful of our older dog's past surgeries and individual needs. We would absolutely book with her again and highly recommend her!

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Erin M.
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
50 reviews
23 repeat clients
20 years of experience
Pasadena, MD, 21122

They took great care of our dog! I appreciated the updates, and he enjoyed playing with their dogs during the week. Thanks for taking great care of our Max!

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Ashley H.
Sitter Profile Image: Alicia D.
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Alicia D.
Star Sitter
from
$50
per night
5.0 out of 5 stars
90 reviews
29 repeat clients
13 years of experience
Bowie, MD, 20716

Booking with Alicia was a fantastic experience! She responded quickly to my last minute request and made my pup feel right at home. She communicated throughout the stay with lots of pictures and updates. My dog has a blast and I highly recommend her!

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

Cat caregivers near you - Rolling Hills

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

Heather did such a great job taking care of our kitties, I think they hardly missed us. She sent us lots of photos while we were away, which was great for peace of mind. We would definitely use Heather again.

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Christine M.
Sitter Profile Image: Bella N.
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Bella N.
Star Sitter
from
$13
per visit
5.0 out of 5 stars
16 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
18 reviews
6 repeat clients
37 years of experience
Annapolis, MD, 21403

Fantastic, very thankful for her help. Will use again!

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Noah M.
Sitter Profile Image: Marley D.
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Marley D.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
41 reviews
14 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: Allison K.
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Allison K.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
285 reviews
126 repeat clients
15 years of experience
Crownsville, MD, 21032

Allison was great and took extra special care with our 2 cats. We unfortunately booked and were away during a snow storm but Allison was able to make all appointments and even used our snow shovel and ice melt to clear our steps which is above and beyond.

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Justin M.
Sitter Profile Image: Jacqueline B.
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Jacqueline B.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
20 reviews
5 repeat clients
30 years of experience
Annapolis, MD, 21401

Jacqueline was fantastic. She came for a meet and greet and Sophia, my cat, took right to her. She followed all my instructions, but she left me with a real sense of comfort that Sophie was going to be in amazing hands. I felt so comfortable while on vacation and I loved the videos and pictures she sent to me. It was a really great experience and she is the only one I will hire in the future.

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Victoria W.
Sitter Profile Image: Corinne C.
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Corinne C.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
31 reviews
6 repeat clients
31 years of experience
Annapolis, MD, 21401

Corinne was very pleasant to work with and took great care of our cats. She even left some extra treats for the cats! Would highly recommend.

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Lucas C.
Sitter Profile Image: Samantha C.
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Samantha C.
from
$15
per visit
5.0 out of 5 stars
26 reviews
9 repeat clients
6 years of experience
Annapolis, MD, 21401

Samantha did a fabulous job of staying at our house and taking care of our cat Duke while we were on vacation. She was even flexible and stayed an additional night at the beginning since we needed to depart a day earlier to avoid any weather delays. She sent daily pictures and kept in touch with us throughout the stay. I recommend her for your pet sitting needs.

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Alison H.
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
7 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: Alexia M.
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Alexia M.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
43 reviews
15 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: Stacie Z.
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Stacie Z.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
22 reviews
5 repeat clients
28 years of experience
Annapolis, MD, 21401

Stacie was super reliable and friendly! Accommodated everything I asked, the pics and videos of my 2 cats were very reassuring while I was away. I will definitely be a repeat client in the future!

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Aamir K.
Sitter Profile Image: Darragh M.
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Darragh M.
from
$17
per visit
5.0 out of 5 stars
37 reviews
12 repeat clients
15 years of experience
Annapolis, MD, 21401

Darragh was absolutely wonderful in caring for our cat while we were away on vacation. He demonstrated remarkable consistency and genuine care throughout. Not only did he spend quality time playing with our cat, providing her with companionship, but he also went above and beyond by voluntarily taking out the trash and tidying our cat's food dish. If you're in search of a reliable and compassionate pet sitter, Darragh is the perfect choice. We wholeheartedly endorse him and eagerly anticipate utilizing his services in the future.

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Larysa T.
Sitter Profile Image: Megan W.
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Megan W.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
71 reviews
34 repeat clients
10 years of experience
Annapolis, MD, 21402

I highly recommend Megan! She is a good communicator and very dependable. She quickly made good friends with my cat Ollie. She took good care of him for three whole weeks without any problems. When I got back, everything was clean and tidy. She was even willing to water my flowers for me. She is an excellent sitter!

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Stan W.
Sitter Profile Image: Gurbata Michelle A.
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Gurbata Michelle A.
from
$18
per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
8 years of experience
Crownsville, MD, 21032

Best cat sitter ever! Michelle went above and beyond. 1000/10 recommend. Our kitties loved her and they’re typically shy. Michelle was attentive, kind, and punctual. She sent the perfect amount of updates and pictures!

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Candice S.
Sitter Profile Image: Ava M.
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Ava M.
Star Sitter
from
$36
per visit
4.9 out of 5 stars
119 reviews
34 repeat clients
18 years of experience
Annapolis, MD, 21401

I'm so thankful to Ava for watching and attending to our Maine Coon. She's extremely dependable and trustworthy. Knowing that our Niki is in good hands while we're on travel is invaluable.

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Dave H.
Sitter Profile Image: Katie F.
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Katie F.
from
$23
per visit
5.0 out of 5 stars
115 reviews
36 repeat clients
16 years of experience
Annapolis, MD, 21401

Katie was a delight to work with. Very friendly and kind, a great communicator. Followed directions perfectly and went above and beyond by collecting our mail and taking out the trash. Would definitely recommend to others.

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Aaron T.
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: Leticia S.
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Leticia S.
from
$14
per visit
5.0 out of 5 stars
6 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: Jazmin G.
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Jazmin G.
from
$21
per visit
5.0 out of 5 stars
29 reviews
6 repeat clients
8 years of experience
21032

Jazmine is awesome!!!!👏

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Vicki S.
Sitter Profile Image: Tori W.
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Tori W.
from
$12
per visit
15 years of experience
Annapolis, MD, 21401

About: With over 15 years of hands on experience caring for animals of all kinds, including dogs, cats, and farm animals, I provide reliable, compassionate care tailored to each pet’s unique needs. I’m comfortable with pets of all ages and personalities, from energetic puppies who need patience and consistency to senior pets who require extra attention and gentle care. I prioritize safety, clear communication, and making sure every pet feels comfortable, loved, and well cared for while you’re away. Whether it’s a fun walk, playtime, or simply keeping your pet company, I’ll treat them like they’re my own.

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Perfect for high energy dogs - Rolling Hills

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: 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: Kacie B.
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Kacie B.
Star Sitter
from
$45
per day
5.0 out of 5 stars
77 reviews
29 repeat clients
12 years of experience
Annapolis, MD, 21401

Kaci was amazing with woody! He loved her company and her dog’s too! They went on multiple trips for woody to play and have fun! We’re truly thankful and grateful for her hard and amazing dog! She was very communicative and very flexible during the whole time, she is phenomenal.

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Brandon D.
Sitter Profile Image: Diana V.
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Diana V.
Star Sitter
from
$55
per day
5.0 out of 5 stars
213 reviews
93 repeat clients
10 years of experience
Riva, MD, 21140

Our pupper enjoyed his day stay and really got to stretch his legs in such a large yard. We received regular updates and felt at ease leaving him in such capable hands.

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Christian M.
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

Lindsay did an amazing job with our Daisy who has separation anxiety. Photo during the day and a fun video to watch. We will book again next time we are in town!

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Debra R.
Sitter Profile Image: Luba & James H.
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Luba & James H.
from
$40
per day
5.0 out of 5 stars
251 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: 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: 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: Dana L.
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Dana L.
Star Sitter
from
$60
per day
5.0 out of 5 stars
35 reviews
15 repeat clients
20 years of experience
Arnold, MD, 21012

Dana is our guardian angel. I am a self proclaimed helicopter mama but I felt completely at easy leaving my little girl. Maddie got to go on a field trip to the garden store and then play in the yard. She couldn’t have been happier which made me happy. We can’t wait to spend another day with Dana and her amazing husband.

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Kate M.
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: Benjamin S.
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Benjamin S.
from
$20
per day
28 years of experience
Severna Park, MD, 21146

About: As a pet lover and owner, I understand the level of care and security pet owners desire. I am patient with pets, understand their needs, and will give them plenty of exercise (as desired) and attention. Whether you need me to visit your pet's home or drop them off at mine, I am glad to help. If you would like me to house your pet, I have plenty of room as well as a fenced in backyard with plenty of room to run. There is also a bike trail nearby I would love to take your pet on if they enjoys walks. I currently have a small dog, but have owned other dogs before as well including a large dog, rabbits, a scorpion, and birds. I'm a quick at responding, so feel free to reach out whenever you may have a pet need. As a student, I have flexible hours and more availability than perhaps the average employee. 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 comfortable home with plenty of indoor and outdoor space, and can make accomodations according to your pet's needs. I have a large basement in addition 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 can provide a regular schedule for your pet to make sure they receive the care that works best for them. As a student, I can provide flexibility in regards to making home visits as well at providing care at my home if desired. I am just looking to help others with their pets. Please let me know any specifics or concerns you may have with what your pet may need.

Sitter Profile Image: Amy D.
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Amy D.
from
$45
per day
5.0 out of 5 stars
28 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: Julia M.
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Julia M.
from
$65
per day
5.0 out of 5 stars
6 reviews
3 repeat clients
4 years of experience
Annapolis, MD, 21401

Julia was fantastic! She treated my puppy with the best care, had great communication and also sent pictures to keep me updated. I definitely will be using her again and I highly recommend her!!

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Joseph T.
Sitter Profile Image: Brittany K.
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Brittany K.
from
$40
per day
5.0 out of 5 stars
129 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: Andy & Lydia M.
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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!

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Anna K.
Sitter Profile Image: Taylor J.
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Taylor J.
from
$38
per day
5.0 out of 5 stars
69 reviews
14 repeat clients
10 years of experience
Annapolis, MD, 21401

Every aspect of working with Taylor was easy and fun. Taylor was very responsive and accommodating. She made an effort to understand Mia’s needs and was very intentional about getting her the exercise she needed for the day. Taylor kept me posted with some photos throughout the day which made me smile. It was obvious that Mia had a blast and was well cared for. I won’t hesitate to reach out to Taylor for doggie day care or boarding in the near future.

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Aj B.
Sitter Profile Image: Celena W.
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Celena W.
Star Sitter
from
$40
per day
5.0 out of 5 stars
12 reviews
4 repeat clients
7 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: Michelle M.
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Michelle M.
Star Sitter
from
$38
per day
5.0 out of 5 stars
557 reviews
258 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.

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Lor K.
Sitter Profile Image: Lucie B.
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Lucie B.
Star Sitter
from
$27
per day
5.0 out of 5 stars
8 reviews
6 repeat clients
8 years of experience
Crofton, MD, 21114

Lucie was absolutely wonderful with my dog! The photos and updates she sent showed just how happy and comfortable he was—his big smiles said it all. It’s clear she genuinely loves and cares for the dogs she watches. I felt completely at ease knowing he was in such great hands. Highly recommend and would definitely book with her again! Thank you so much!

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Amaryllis F.
Sitter Profile Image: Julia H.
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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.

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Natalie K.
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Adventure-ready dog walkers - Rolling Hills

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: 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: Heather B.
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Heather B.
Star Sitter
from
$28
per walk
5.0 out of 5 stars
164 reviews
52 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: Marley D.
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Marley D.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
41 reviews
14 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: Megan W.
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Megan W.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
71 reviews
34 repeat clients
10 years of experience
Annapolis, MD, 21402

Megan is fantastic. Prompt and really communicative and Zap was excited for a walk every time she comes. Will be booking Megan again for sure.

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Britton W.
Sitter Profile Image: Delaney B.
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Delaney B.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
9 reviews
2 repeat clients
3 years of experience
Arnold, MD, 21012

About: Hi there! I'm Delaney. Over the past year, I have fostered 2 dogs and 6 cats! Each foster was a new learning experience, gaining insight into animals boundaries and needs! Often having sick or injured rescue fosters, I have experience with giving topicals and oral medications. I have always had dogs, dealing with puppies up until elderly care. For many years I have been a sitter for my neighbors 2 cats and one dog. It has become a passion to help and take care of dogs and cats, and I hope to be everything you need for a pet sitting experience! I will be heading back to Columbia SC on August 16th and won’t be in Annapolis for pet sitting anymore! I am available all summer long, the only time I am unavailable is 9am to 12pm Monday, Tuesday, and Wednesday, while I am taking an EMT class at AACC! I usually wake up early, so I’ll be available before and after this class!! I am very active, love to take long walks or runs. I am very open to following pet owners lead. Often staying in their own home is often better for a pets routine to reduce stress. I am available to give pets company during daytime, and if needed overnight. I know how stressful being away from your pet is, and sending updates is crucial!! I am very communicative, respectful, and clean.

Sitter Profile Image: Alexia M.
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Alexia M.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
43 reviews
15 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: Kacie B.
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Kacie B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
76 reviews
29 repeat clients
12 years of experience
Annapolis, MD, 21401

Kacie was so sweet to my pup! She sent a lot of updates on how my dog was doing and gave her so much attention. I couldn’t have asked for anyone better to help out with my baby

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Stephanie G.
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
6 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: 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: Mackenzie C.
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Mackenzie C.
from
$15
per walk
5.0 out of 5 stars
11 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: Cade S.
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Cade S.
from
$15
per walk
5.0 out of 5 stars
3 reviews
2 repeat clients
5 years of experience
Annapolis, MD, 21409

Cade did a fantastic job! Hendricks had a blast. He was right on time and took great care of our pup! Definitely will be having him help us again with Hendricks!

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Julianne H.
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
7 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: Sarah M.
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Sarah M.
from
$15
per walk
20 years of experience
Annapolis, MD, 21401

About: Besides my own dogs that I have taken care of since I was very young, I also have been relied on to take care of family and neighbor dogs. Most dogs that I have cared for have been geriatric, and I am extremely patient with them, and strong enough to even lift the larger dogs when they can’t lift themselves. Before coming to MD, I worked on a farm and interacted with dozens of dogs every day. I have never met a dog that hasn’t liked me, or one I haven’t liked. I work from home and so can easily step out for a drop-in or house sit and work from your home. I can do early morning or late evening according to need. I am unable to board your dogs. However, I am more than able to watch your dogs in your home. When in a client’s home, my philosophy is to only touch what is needed. The client’s direction and privacy is key to a good relationship, as well as my discretion.

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: 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: Katie F.
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Katie F.
from
$20
per walk
5.0 out of 5 stars
115 reviews
36 repeat clients
16 years of experience
Annapolis, MD, 21401

Katie was wonderful in every way!

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Nadia N.
Sitter Profile Image: Amber C.
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Amber C.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
56 reviews
17 repeat clients
12 years of experience
Annapolis, MD, 21401

Amber was absolutely awesome. She walked our dog Cisco for a few days during the week when I was out of town on business and my wife was working late in DC. She was on time, she was kind and she even dried her paws off when it was a rainy day. We will definitely be using her services again! Thank you Amber.

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

Samantha was great with DaVinci

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Chris A.
Sitter Profile Image: Mateo V.
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Mateo V.
from
$15
per walk
10 years of experience
Annapolis, MD, 21401

About: I’ve cared for my own dog for the past 3 years, giving me daily, real‑world experience with feeding routines, walks, training, and managing anxiety. I’m patient, attentive, and committed to keeping pets safe, comfortable, and happy while their people are away. I work during the day, but I’m available for pet care in the afternoons, evenings, weekends, and on most holidays. I make time to ensure every pet gets plenty of attention, exercise, playtime, bathroom breaks, and companionship while they’re in my care. I’ve owned my own dog for the past three years and have experience living with two dogs and three cats, so I’m comfortable caring for pets with different personalities and needs. I prioritize their safety by following your care instructions, maintaining their feeding and potty schedules, keeping a clean and secure environment, and providing plenty of supervision, affection, and exercise. I’ll also keep you updated with photos and messages so you know your pet is happy and well cared for.

Sitter Profile Image: Tori W.
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Tori W.
from
$20
per walk
15 years of experience
Annapolis, MD, 21401

About: With over 15 years of hands on experience caring for animals of all kinds, including dogs, cats, and farm animals, I provide reliable, compassionate care tailored to each pet’s unique needs. I’m comfortable with pets of all ages and personalities, from energetic puppies who need patience and consistency to senior pets who require extra attention and gentle care. I prioritize safety, clear communication, and making sure every pet feels comfortable, loved, and well cared for while you’re away. Whether it’s a fun walk, playtime, or simply keeping your pet company, I’ll treat them like they’re my own.

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

Large dog specialists near you - Rolling Hills

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

Another stay with Carlie and we cannot recommend her enough! We always have such peace of mind with her daily updates and photos and knowing that our pup, Indi, is safe and having fun. Indi gets her own vacation when she stays here and we love knowing that our she gets to enjoy herself, too! Between Carlie's loving and kind family, the huge bonus yard, and Carlie's attention and ability to continue medicine (she even notices any behavioral changes!), we just know we've made the right choice. Do yourself a favor, and get on her schedule for your pup sitting needs! :)

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Kyanna B.
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

Yukia did a fantastic job with our dog, Sammy! Communication regarding pickup and drop off was excellent and we got some pictures of Sammy on a regular basis. Would definitely book with Yukia again!

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Stephen G.
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

This was Balee's first boarding stay with Mady. She and her family were Ah-Mazing! I felt bad leaving because of an ear infection that he was diagnosed with a day before our departure. Balee received lots of TLC during his visit and Mady kept me updated about his adjustment daily (which was comforting).

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Temeka P.
Sitter Profile Image: Kimberly W.
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Kimberly W.
from
$45
per night
5.0 out of 5 stars
51 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!

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Hayley M.
Sitter Profile Image: Hester D.
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Hester D.
from
$38
per night
5.0 out of 5 stars
6 reviews
1 repeat client
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: Gurbata Michelle A.
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Gurbata Michelle A.
from
$30
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
20 years of experience
Odenton, MD, 21113

Ahhhmazing!!! Michelle will absolutely be our go to dog sitter! Oliver is still a puppy so he is high energy and still working on his potty training. This was our first time using rover and his first time away from us. Michelle took care of him above and beyond our expectations! She sent us model pictures of him daily (much better than he lets us take of him, so we have new profile pics of him, lol!) She provided daily updates with the pics too, all of which gave us complete peace of mind! We couldn’t have had a better experience and that made our vacation that much more relaxing. We are extremely thankful to Michelle for treating Oliver like her own! 😊

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Destanie S.
Sitter Profile Image: Elena K.
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Elena K.
Star Sitter
from
$40
per night
5.0 out of 5 stars
17 reviews
3 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: Candice W.
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Candice W.
Star Sitter
from
$65
per night
5.0 out of 5 stars
100 reviews
35 repeat clients
14 years of experience
Annapolis, MD, 21409

We highly recommend Candice! She will love your pup as her own! She took great care of our pup and sent lots of photos. She has a big yard and room for the pups as well! Our dog also has a bit of energy so it was perfect that he could play with her pup as well. He came home worn out and well loved!!

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Matt & Taylor T.
Sitter Profile Image: Carla B.
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Carla B.
from
$40
per night
5.0 out of 5 stars
5 reviews
12 years of experience
Severna Park, MD, 21146

We had a wonderful experience boarding our pup in Carla's home! Our dog was so well cared for, and Carla sent daily updates with pictures and videos. Her dog was incredibly sweet and got along great with ours. She did a great job balancing exercise with being mindful of our older dog's past surgeries and individual needs. We would absolutely book with her again and highly recommend her!

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Erin M.
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
50 reviews
23 repeat clients
20 years of experience
Pasadena, MD, 21122

They took great care of our dog! I appreciated the updates, and he enjoyed playing with their dogs during the week. Thanks for taking great care of our Max!

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Ashley H.
Sitter Profile Image: Justine P.
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Justine P.
from
$55
per night
5.0 out of 5 stars
65 reviews
30 repeat clients
31 years of experience
Pasadena, MD, 21122

Absolutely wonderful dog sitter! My pup was well cared for and loved while I was away. Great communication and plenty of updates. Highly recommend!

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Kirsten O.
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: Celena W.
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Celena W.
Star Sitter
from
$50
per night
5.0 out of 5 stars
12 reviews
4 repeat clients
7 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: Brittany K.
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Brittany K.
from
$40
per night
5.0 out of 5 stars
131 reviews
58 repeat clients
20 years of experience
Severna Park, MD, 21146

Brittany was FANTASTIC. This was my first time using Rover so she sent me a comprehensive list of items that I should send with my dog, Coco, along with a few other recommendations. She was super responsive, and sent daily pictures and updates. Coco had so much fun running around with the other dogs and playing with Brittany’s kiddos that she slept a whole day after returning back home! We will definitely be using Brittany again in the future.

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

Thomas & Melissa cared for Korey for one night while I was away and I could tell Korey had a great time! Korey will be staying with them again for 10 days next month.

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Kelly H.
Sitter Profile Image: Sari S.
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Sari S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
12 reviews
5 repeat clients
30 years of experience
Millersville, MD, 21108

We have had Sari watch Rusty twice now and she has done an amazing job! It was a weight off of my shoulders going into the second time because I knew he'd be well taken care of and have a great time with her. She does incredible long walks and even took him to a park on the water, which was a new experience for him! I cannot recommend Sari enough.

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Tim and Johanna F.
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
15 repeat clients
20 years of experience
Arnold, MD, 21012

Dana took my pup Dillon for a few overnights when I went out of town recently, and he had the best time! She sent frequent photo updates of his adventures, and it was clear that she cared for him like he was her own. The fenced-in back yard was perfect for this city boy to stretch his legs! 🐾

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Cheryl C.
Sitter Profile Image: Anya B.
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Anya B.
from
$25
per night
5.0 out of 5 stars
4 reviews
1 repeat client
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: 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

I recently had my first booking with Peggy and the entire process from meeting her to updates throughout Starbuck's stay was exceptional. It was very easy to schedule drop off and pick up times and she was easy to reach. Starbuck was completely comfortable in her home and in her care. I am so happy I chose Peggy for Starbuck's sitter needs and will be using her services in the future!

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Ashley M.
Sitter Profile Image: Marta F.
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Marta F.
from
$60
per night
5.0 out of 5 stars
47 reviews
23 repeat clients
17 years of experience
bowie, MD, 20715

Marta has become our go-to day care provider and boarder, and we consider ourselves incredibly fortunate to have found her. Our dog, Miss Charlie, has stayed with Marta approximately five times now, including the recent Thanksgiving holiday. Each time, Charlie has had a fantastic experience. This last time included a wonderfully special Thanksgiving meal featuring turkey and sweet potatoes! As an overly protective dog mom, finding someone who cares for your pup as much as you do can be challenging. However, I can confidently say that Marta loves our dog just as much as we do. We have complete trust in her, and her professional-quality pictures not only keep us informed but also make us miss our pup even more—they are so cute! If you're in search of an exceptional sitter for your pup, look no further. Marta is, without a doubt, the best choice. We highly recommend her!

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Monique S.
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1Global data from Rover (November 2025)