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.

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
139 reviews
61 repeat clients
8 years of experience
Annapolis, MD, 21401

Shuling was amazing! She sent us pictures and videos the whole time and made it easier to be apart from our pup. Bailey had a great time playing with the host’s dog and family. Honestly, it looked like a summer camp for the doggies :) 100% recommend her and will use her services again. Jake and Ana

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

Carlie took such wonderful care of our 11 year old Golden. She and her children spoiled him with all kinds of love and attention. I felt very comfortable leaving him while we were on a week long vacation.

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Carolyn R.
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

Very pleased with how thoughtful and caring Katelyn and Blaze were with our dog. Katelyn provides frequent communication, photos and video. I highly recommend and will surely be back.

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Henry G.
Sitter Profile Image: Michelle M.
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Michelle M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
555 reviews
257 repeat clients
25 years of experience
Annapolis, MD, 21409

Michelle did a great job watching my little guy Charlie. She went out of her way to make him feel at home. She sent me much-appreciated pics and texts to let me know he was doing fine. I look forward to using her again!

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Teresa C.
Sitter Profile Image: Katie F.
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Katie F.
from
$45
per night
5.0 out of 5 stars
114 reviews
36 repeat clients
16 years of experience
Annapolis, MD, 21401

Thanks for taking good care of our Murphy while we explored Baltimore for a bit. It was easier dropping him off instead of keeping him penned up in a hotel room not knowing how he’d be. Thanks so much!

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Lori L.
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

Sakura stayed for 7 days while we were away and did great. She was clearly well cared for, and we loved receiving pictures and updates throughout the stay. She seemed happy and settled, which says a lot. We’d definitely book again.

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Takako L.
Sitter Profile Image: Diana V.
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Diana V.
Star Sitter
from
$57
per night
5.0 out of 5 stars
206 reviews
88 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: 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: Nadia H.
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Nadia H.
from
$42
per night
5.0 out of 5 stars
55 reviews
25 repeat clients
5 years of experience
Odenton, MD, 21113

Nadia was super nice a took great care of my Lizzie. She understood her social anxiety and accompanied her beautifully. Would definitely use her again.

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Ongela 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

Mady is always a joy to work with! Kiko gets so excited to go over to her house and play with Bandit which is a testament to Mady’s care and attention! Kiko can’t wait to go back!

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Hannah K.
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
18 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: 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

Our first time boarding with Shelby was a great experience! She was flexible, communicative, and followed all care instructions for our dog Loki. Will definitely be calling her up in the future.

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Trevin B.
Sitter Profile Image: ANGELA B.
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ANGELA B.
Star Sitter
from
$40
per night
5.0 out of 5 stars
17 reviews
3 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: 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: Megan H.
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Megan H.
Star Sitter
from
$43
per night
4.9 out of 5 stars
54 reviews
14 repeat clients
10 years of experience
Odenton, MD, 21113

Amazing!! First timer here and was very nervous about leaving our baby, but Megan made sure to send us videos and photos and keep us updated. She was very nice and she took great care of our fur baby!

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Jessica 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
47 reviews
23 repeat clients
20 years of experience
Pasadena, MD, 21122

Wonderful that she sends updates with pictures of Dan while I’m out of town. She was very flexible about what time I picked him up from boarding when my flight came in earlier than expected.

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David P.
Sitter Profile Image: Carla B.
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Carla B.
from
$31
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: 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 took great care of my two dogs. She sent regular updates and photos 3 times a day. She invited them everywhere in her home so I knew they were part of the family. She had her own dog plus a couple of other regulars who all got along great and played well with each other. One of my dogs did not cooperate and had a few accidents. Candice could not have been nicer about it. I would definitely use Candice again.

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Kirsten C.
Sitter Profile Image: Beth H.
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Beth H.
Star Sitter
from
$68
per night
5.0 out of 5 stars
56 reviews
17 repeat clients
40 years of experience
Edgewater, MD, 21037

Beth is excellent! She put my mind at ease. I felt extremely comfortable with my fur baby in her care. She kept me informed and even provided pictures! I will definitely reach out with future needs!

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kelly f.
Sitter Profile Image: Jasmine A.
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Jasmine A.
Star Sitter
from
$35
per night
5.0 out of 5 stars
64 reviews
29 repeat clients
8 years of experience
Odenton, MD, 21113

Jasmine was very flexible. She took great care of our pup and sent us awesome pics throughout her stay. We look forward to working with her more.

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Nicole R.
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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
155 reviews
51 repeat clients
17 years of experience
Annapolis, MD, 21401

Heather did a fabulous job with my sweet Luna. Luna even came out for her and hung out with Heather! :) I appreciate her following all my instructions and letting me know how Luna was doing!

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

Corinne was wonderful! Our cat can be a bit spicy but Corinne didn’t take it personally & still took such good care of her. We will 100% rebook with Corinne for any future care needed for our cat!

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Kourtney C.
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: Marley D.
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Marley D.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
32 reviews
13 repeat clients
15 years of experience
Annapolis, MD, 21401

Great communication and kept my Velcro cat company during Christmas! Thank you for helping with the food bowls and the “presents” and meds!

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

Jacki was superb! She thoughfully sent photos of Shelly every day. The. house was as clean as a whistle and everything was just as perfect as should be. I would have Jacki back in a heartbeat if she were available.

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

Jazmine is awesome!!!!👏

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Vicki S.
Sitter Profile Image: Stacie Z.
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Stacie Z.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
21 reviews
5 repeat clients
28 years of experience
Annapolis, MD, 21401

Stacie was great and I’d absolutely book with her again. She was flexible, communicative, and clearly took great care of my cats while I was away. She went above and beyond to make sure everything was handled, kept me updated, and gave me real peace of mind during my trip. It was obvious from the updates and from how my cats acted afterward that they were comfortable with her and well cared for. I really appreciated her attention to detail and the care she put into everything. Highly recommend.

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Alexander W.
Sitter Profile Image: Katie F.
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Katie F.
from
$18
per visit
5.0 out of 5 stars
114 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: Alexia M.
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Alexia M.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
37 reviews
13 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: 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: Leigh Ann E.
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Leigh Ann E.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
14 reviews
5 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: Allison K.
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Allison K.
from
$20
per visit
4.9 out of 5 stars
281 reviews
125 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: Courtney A.
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Courtney A.
Star Sitter
from
$26
per visit
5.0 out of 5 stars
14 reviews
4 repeat clients
15 years of experience
Edgewater, MD, 21037

Courtney was absolutely amazing. She sent plenty of photos along with thoughtful, detailed updates, and my cat clearly adored her. I’m so grateful for her — especially for being so flexible on such short notice. I would book her again in a heartbeat, 1000%!

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Ashlee B.
Sitter Profile Image: Bella N.
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Bella N.
from
$13
per visit
5.0 out of 5 stars
15 reviews
2 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: Ava M.
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Ava M.
Star Sitter
from
$36
per visit
4.9 out of 5 stars
118 reviews
33 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: Samantha C.
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Samantha C.
from
$15
per visit
5.0 out of 5 stars
25 reviews
8 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: 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

We had an excellent experience with Andrew caring for our two cats. He provided thoughtful updates, followed all instructions perfectly, and made us feel completely at ease while we were away. Our cats were happy, comfortable, and clearly well looked after. We’re so grateful for his care and would highly recommend him to anyone needing a dependable sitter.

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Allison M.
Sitter Profile Image: Whitney B.
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Whitney B.
from
$23
per visit
5.0 out of 5 stars
60 reviews
21 repeat clients
14 years of experience
Annapolis, MD, 21401

Whitney made us feel so comfortable boarding our cat with her! She sent frequent photos updates and we always knew he was in good hands. Thank you so much Whitney!

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

Megan was absolutely amazing with my cat Frankie! Not only did she follow all of his instructions, but she went above and beyond to do extra, including stay for longer scheduled visits than I had booked, solely because I had expressed Frankie’s need for a little extra company at night. Megan is attentive, caring, a quick responder, and overall an amazing sitter. I will 100% be booking with her again in the future. Frankie says thank you too :)

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

Olivia has been great with our two cats! Very responsive, sent plenty of pictures and video, and the cats LOVED her. Would definitely ask her to take care of our babies again. Thank you Olivia!

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Chris B.
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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: Kacie B.
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Kacie B.
Star Sitter
from
$45
per day
5.0 out of 5 stars
74 reviews
28 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: 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

Alex Z. was amazing! Very loving and caring while dog sitting for my 3 month old puppy. Her pets were loving and playful also. She took lots of pics and kept me updated with his activities throughout the day. Will definitely request her services again.

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Melissa M.
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
88 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: 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: Lindsay M.
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Lindsay M.
Star Sitter
from
$55
per day
5.0 out of 5 stars
46 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: 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: 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: 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: 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

Dana was great. We needed someone close to my sister's house while we celebrated an early Christmas, and she was able to help us out. We will definitely use her again when we are in town.

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Jennifer B.
Sitter Profile Image: Blake K.
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Blake K.
from
$45
per day
5.0 out of 5 stars
3 reviews
10 years of experience
Annapolis, MD, 21401

About: I have had dogs my whole life! My golden just recently passed and I currently have a 4 year old Australian Shepherd. I would love to walk and take care of your dog. Our current dog Bodie would also love to have friends to play with! Most of my experience is with bigger dogs but I am open to smaller dogs as well. I live in a neighborhood that is dog friendly and there are plenty of dogs around for fun interaction and play time if the dog is allowed! My schedule is open and flexible. I work in and out of the office weekly but can accommodate most schedules! Will only accept what I’m able to do! I love going on long walks. Pets are treated like humans in our household. We love animals so much and can’t wait to take care of your pet.

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.
Sitter Profile Image: Lucie B.
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Lucie B.
Star Sitter
from
$27
per day
5.0 out of 5 stars
6 reviews
4 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: Laura T.
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Laura T.
from
$40
per day
5.0 out of 5 stars
36 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: Amy D.
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Amy D.
from
$45
per day
5.0 out of 5 stars
27 reviews
11 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: Moriah C.
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Moriah C.
from
$50
per day
20 years of experience
Annapolis, MD, 21401

About: I’ve had cats and dogs since I was young. I’m very caring and have a soft spot for animals. Excited to be apart of your pets care! I only work 3 days a week so have lots of time to spend with your pet. I’m very outgoing and love to care animals My own pets are very well kept, I take them to the vet on time and always keep them clean/my home clean. In others homes I make sure I am there and punctual and give your pet all the attention they need

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

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

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Melissa S.
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: Michelle M.
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Michelle M.
Star Sitter
from
$38
per day
5.0 out of 5 stars
555 reviews
257 repeat clients
25 years of experience
Annapolis, MD, 21409

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

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Lor K.
Sitter Profile Image: Luba & James H.
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Luba & James H.
from
$40
per day
5.0 out of 5 stars
247 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: Brittany K.
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Brittany K.
from
$40
per day
5.0 out of 5 stars
124 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.
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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: Marley D.
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Marley D.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
32 reviews
13 repeat clients
15 years of experience
Annapolis, MD, 21401

I selected Marley as a back-up to my regular walker. She has been professional, dependable, flexible, and fun for my puppy. I would highly recommend her and plan to use her much more in the future!

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Kathy G.
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: Sylvie L.
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Sylvie L.
from
$17
per walk
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: Courtney A.
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Courtney A.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
14 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: Kacie B.
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Kacie B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
74 reviews
28 repeat clients
12 years of experience
Annapolis, MD, 21401

Kacie is a lifesaver! My dogs are notoriously high-energy and can be a handful, but they absolutely adored her. She was patient, understanding, and knew just how to handle their quirks. I came home to happy, well-exercised pups, and I could tell they had a blast with Kacie. I'm so grateful for her reliable and professional service. I highly recommend her to anyone looking for a dog walker who can handle even the most challenging furry friends!

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Tommy C.
Sitter Profile Image: Heather B.
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Heather B.
Star Sitter
from
$28
per walk
5.0 out of 5 stars
155 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: Katie F.
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Katie F.
from
$20
per walk
5.0 out of 5 stars
114 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: 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: Chelsea F.
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Chelsea F.
from
$15
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: Owen K.
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Owen K.
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: 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: 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: Nolan C.
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Nolan C.
from
$15
per walk
8 years of experience
Annapolis, MD, 21409

About: I have taken care of different types of dogs and including in home stay, walks, puppies etc. I have lots of experience in caring for animals from reptiles to mammals. 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 have an invisible fence with a front and back yard, two parks that allow dogs in my neighborhood including water access. I have open space in the home and can easily follow any typical rules or care needs for your pet

Sitter Profile Image: Bella N.
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Bella N.
from
$16
per walk
5.0 out of 5 stars
15 reviews
2 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: Rosalie H.
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Rosalie H.
from
$15
per walk
5 years of experience
Crownsville, MD, 21032

About: I have always loved caring for all animals. From a young age I choose to take on the responsibilities of managing my families dog and now wish to provide loving care for dogs in my community. Everything from walks, to potty breaks, to play time, I will strive to bring premium care to the furry friends you have in your family! I have lots of flexibility regarding pet care. I can help weekends, weekdays, mornings, nights whatever fits best for your family I will try my hardest to accommodate! Pets are family and I strive to treat them with the utmost care and respect while tending to their needs. I always make sure to fully understand every specific need a pet has provideding unique care for each pet. Wether it’s a long walk, feeding particular foods, brushing a long coat, taking potty breaks etc. I will give each individual pet proper attention, and insure they have a positive experience under my supervision.

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

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

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

About: I have had 10 years of personal experience with dogs of varying sizes and cats as well. I have a golden retriever myself as well as a burmese cat back at home in Virginia! I have no allergies to dogs or cats. I am comfortable with picking up after animals if need be;) as well as taking care of more than one animal at once. I have reliable transportation to and from location. Will leave notes if anything happens, and will send lots of pictures if wanted! You can trust me to love and care about your furry friends! I always have my phone on me if any concerns or needs may come up or change. I live in an apartment with a huge courtyard that is fenced in where your pets can run and play! Thank you!

Sitter Profile Image: Taylor J.
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Taylor J.
from
$31
per walk
5.0 out of 5 stars
69 reviews
14 repeat clients
10 years of experience
Annapolis, MD, 21401

Taylor was so awesome! My Great Dane is tough to find a walker for and Taylor was so great with him. He had so much fun on their walks together and I felt very comfortable leaving him in her care. 10/10 would recommend

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Tess T.
Sitter Profile Image: Allison K.
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Allison K.
from
$21
per walk
4.9 out of 5 stars
281 reviews
125 repeat clients
15 years of experience
Crownsville, MD, 21032

Allison is an excellent dog walker. She is very attentive to our dog’s needs. She spends an hour to walk and play with Duke while we are at work. Allison leaves very thorough reports after each walk and communicates if any scheduling updates are needed for the week ahead. We really appreciate having Allison spend time with our dog and we would absolutely recommend her to others. Thank you.

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Christopher M.
Sitter Profile Image: Lily K.
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Lily K.
from
$20
per walk
5.0 out of 5 stars
2 reviews
2 repeat clients
10 years of experience
Annapolis, MD, 21401

Lily was courteous, timely and wonderful to work with. Our Dog was not in a good place when she started working with us , moving anxiety. Lily was patient and flexed as needed to make it work!!

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Michel H.
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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.

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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
69 reviews
28 repeat clients
15 years of experience
Severna Park, MD, 21146

Carlie took such wonderful care of our 11 year old Golden. She and her children spoiled him with all kinds of love and attention. I felt very comfortable leaving him while we were on a week long vacation.

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Carolyn R.
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

Sakura stayed for 7 days while we were away and did great. She was clearly well cared for, and we loved receiving pictures and updates throughout the stay. She seemed happy and settled, which says a lot. We’d definitely book again.

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Takako L.
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: 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

Mady is always a joy to work with! Kiko gets so excited to go over to her house and play with Bandit which is a testament to Mady’s care and attention! Kiko can’t wait to go back!

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Hannah K.
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

Our first time boarding with Shelby was a great experience! She was flexible, communicative, and followed all care instructions for our dog Loki. Will definitely be calling her up in the future.

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Trevin B.
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: Jillian & Richard A.
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Jillian & Richard A.
Star Sitter
from
$49
per night
5.0 out of 5 stars
47 reviews
23 repeat clients
20 years of experience
Pasadena, MD, 21122

Wonderful that she sends updates with pictures of Dan while I’m out of town. She was very flexible about what time I picked him up from boarding when my flight came in earlier than expected.

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David P.
Sitter Profile Image: Carla B.
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Carla B.
from
$31
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: 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 took great care of my two dogs. She sent regular updates and photos 3 times a day. She invited them everywhere in her home so I knew they were part of the family. She had her own dog plus a couple of other regulars who all got along great and played well with each other. One of my dogs did not cooperate and had a few accidents. Candice could not have been nicer about it. I would definitely use Candice again.

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Kirsten C.
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: Megan T.
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Megan T.
from
$33
per night
5.0 out of 5 stars
5 reviews
4 years of experience
Annapolis, MD, 21403

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

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Rob C.
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 absolute best rover sitter! She loves and cares for your dogs as if they were her own. Always communicative and goes the extra mile to take care of your pets.

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Kaliyah S.
Sitter Profile Image: Riley N.
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Riley N.
from
$60
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
17 years of experience
Annapolis, MD, 21401

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

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Mackenzie G.
Sitter Profile Image: Becca K.
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Becca K.
Star Sitter
from
$50
per night
5.0 out of 5 stars
31 reviews
9 repeat clients
20 years of experience
Pasadena, MD, 21122

Becca did a fantastic job taking care of Nami! I’m always a bit apprehensive when trying a new sitter, but she quickly put my mind at ease. Nami got plenty of walks and Becca really took the time to understand her personality. I really appreciated all the photo updates and regular check-ins—they made a big difference. Her son was also very sweet and gentle with Nami, which was lovely to see. I would definitely book with Becca again!

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Kathy L.
Sitter Profile Image: Dana P.
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Dana P.
Star Sitter
from
$65
per night
5.0 out of 5 stars
63 reviews
19 repeat clients
30 years of experience
Crofton, MD, 21114

Dana was great with our 2 older but very active pitties. We're always a bit worried with a new sitter but she went above and beyond to make us (and them) feel comfortable and relaxed while we were gone. They loved being around her kids too which is a plus since they rarely get to play with kids anymore. We'll definitely use her again!

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

Sari did an amazing job with Rusty! From the drop off I could tell she was incredibly attentive to his needs and getting him comfortable in her home. She did an excellent job keeping us updated throughout his stay. If your dog loves long walks, you MUST book Sari. She said over his 4 day stay, she walked him at least 18 miles. He came back happy and relaxed.

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Tim and Johanna F.
Sitter Profile Image: Kacie B.
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Kacie B.
Star Sitter
from
$65
per night
5.0 out of 5 stars
74 reviews
28 repeat clients
12 years of experience
Annapolis, MD, 21401

We used Kacie for two nights of dog boarding and she was awesome! Excellent communication, sent lots of photos/videos, daily walks and dog park visits. Our dog was in good hands and it was obvious he enjoyed his time with Kacie and Blu. We will definitely be booking with Kacie again and highly recommend her to anyone else.

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Kyle A.
Sitter Profile Image: Anya B.
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Anya B.
from
$25
per night
8 years of experience
North Beach, Annapolis, MD, 21401

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

Sitter Profile Image: 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 felt very comfortable leaving my dog with her, and would definitely use her service again. She was very nice and kind. Very warm and set my heart at ease the minute i walked in her door.

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Tess R.
Sitter Profile Image: Kendall L.
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Kendall L.
from
$50
per night
5.0 out of 5 stars
5 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.
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