Pet Sitting in Chestertown

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Sitter Profile Image: kailey f.
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Sitter Profile Image: kailey f.
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1. kailey f.

Star Sitter
every pet deserves equal love!
Annapolis, MD, 21409
23.3 mi. away
Drop-In Visits, Dog Walking
from
$19
per visit
5.0 out of 5 stars
13 reviews
5 repeat clients
Profile image

Reliable and good communication! Happy pets!

Availability updated 2 days ago
Sitter Profile Image: Rebeka C.
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Sitter Profile Image: Rebeka C.
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2. Rebeka C.

In school for dog training!
Chester, MD, 21619
19.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$13
per visit
5.0 out of 5 stars
14 reviews
2 repeat clients
Profile image

Rebeka is Fabulous. Will use her service again.

Availability updated 79 days ago
Sitter Profile Image: Lauren B.
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Sitter Profile Image: Lauren B.
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3. Lauren B.

Dedicated Pet Lover
Centreville, MD, 21617
12.0 mi. away
Drop-In Visits, Dog Walking
from
$15
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
Profile image

Lauren was a perfect sitter for our cats and fish. She came by for a meet and greet before we left and gave us updates while we were away. Our pets seemed totally unbothered by our absence, and everything was in great shape when we returned. Would absolutely recommend her to anyone and would be delighted to have her back.

Availability updated 7 days ago
Sitter Profile Image: Mariah W.
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Sitter Profile Image: Mariah W.
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4. Mariah W.

Star Sitter
Always play time !
Edgewood, MD, 21040
20.4 mi. away
Drop-In Visits, Dog Walking
from
$16
per visit
5.0 out of 5 stars
125 reviews
35 repeat clients
Profile image

If I could leave more than 5 stars, I absolutely would. Mariah not only took excellent care of my 2 kittens while I was away for the holidays, but she helped save my home from a disaster. A pipe froze and burst while I was out of town and she took immediate action when she discovered the flooding in my home. She called the county water authority to have them assess the issue, ensured the main was turned off, and even brought water from her own home for my cats since there was no longer running water at my house. She offered her time and flexibility since she was local and I was out of state, and I am so grateful yo her. I could not have asked for a better person to be there. Thanks so much Mariah!

Availability updated 4 days ago
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Marissa F.
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Sitter Profile Image: Marissa F.
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5. Marissa F.

Star Sitter
Pet mama to the rescue
Chestertown, MD, 21620
5.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
5.0 out of 5 stars
20 reviews
9 repeat clients
Profile image

Marissa was incredibly professional! My cat was well taken care of during my 5 day business trip! Marissa followed all my instructions carefully and had immaculate attention to detail! My cat was very happy with her and not stressed when I returned home! Marissa was easy to communicate and work with! Absolutely would recommend her and I hope she will cat-sit for me in the future! She even accommodated me when I messed up meeting with her the first time! She’s the best.

Availability updated 67 days ago
Sitter Profile Image: Taylor M.
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Sitter Profile Image: Taylor M.
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6. Taylor M.

Stress-Free Companionship
Stevensville, MD, 21666
19.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$10
per visit
1 review
1 repeat client

I am very happy with the care Taylor provided for both my home and my cats! I have used her for many years including when I used to have a dog. Taylor always communicates clearly and promptly before, during, and after the stay. Two of my cats, are shy around new people, but Taylor was incredibly patient and attentive, and eventually earned their trust. Taylor made sure to follow all the instructions I provided, and even sent me regular updates and pictures, which I really appreciated. She also brought in my mail and watered my plants. The house was left in great condition when I returned—clean, organized, and exactly as I left it. Taylor went above and beyond in making sure both my cats and home were well taken care of. I highly recommend Taylor to anyone looking for a responsible and reliable pet and house sitter. I already have her booked for two more upcoming trips.

Availability updated 22 days ago
Sitter Profile Image: Mikeyla A.
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Sitter Profile Image: Mikeyla A.
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7. Mikeyla A.

Happy Wagging Tails Start Here!
Edgewood, MD, 21040
20.0 mi. away
Drop-In Visits, Dog Walking
from
$17
per visit
4.7 out of 5 stars
5 reviews
Profile image

Mikeyla took great care of my dog while we were away! She went above and beyond! It was so nice not having to worry about our dog. We will definitely be using her services again!

Availability updated 5 days ago
Sitter Profile Image: Brittany B.
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Sitter Profile Image: Brittany B.
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8. Brittany B.

Love Your Doggos
Aberdeen Proving Ground, MD, 21005
19.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$13
per visit
5.0 out of 5 stars
1 review
1 repeat client

About: I’ve taken care of dogs of all kinds since I was about 13. Recently I have taken it more serious in the past years. I’ve owned 3 dogs, a puggle, golden retriever and a pit bull mix. A lot of my family and friends rely on me to walk and feed their pets. I have recently dog sat for my friends who have two beautiful Great Danes. I also dog sat and house sat for my boss who owns a husky and a pit mix. They were absolutely amazing! I’m super good with any age dog. I’m willing to make the proper accommodations for any older doggos as well as puppies if need be. I honestly just love animals especially dogs. I do love sitting cats as well. I’m currently in the Army, stationed at Aberdeen Proving Ground. I work Mon-Fri from 6:30am-4:00pm. Some weekends, I do get 3 or 4 day weekends. I can come by during lunch if need be. I am available to stay the night at your house if need be whether it be on or off post. I’m willing to travel as well. I do live on post in barracks housing. So it is difficult for me since i cannot bring pets to my home. However I’m willing to go to dog parks or anywhere that you need me to go.

Availability updated 4 days ago
Sitter Profile Image: Beverly H.
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Sitter Profile Image: Beverly H.
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9. Beverly H.

Your dogs new best friend!
Queenstown, MD, 21658
16.9 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
4 reviews
Profile image

Beverly was great with our dog Ace.

Availability updated 4 days ago
Sitter Profile Image: Tori V.
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Sitter Profile Image: Tori V.
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10. Tori V.

Caring animal lover
Centreville, MD, 21617
6.7 mi. away
Drop-In Visits, Dog Walking
from
$25
per visit
5.0 out of 5 stars
6 reviews
3 repeat clients
Profile image

Tori was great!! Super accommodating, took great care of the pets, & kept us updated throughout the weekend!

Availability updated 41 days ago
Sitter Profile Image: Shaun C.
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Sitter Profile Image: Shaun C.
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11. Shaun C.

Hi! I'm Shaun and I love animals!
Chestertown, MD, 21620
1.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$12
per visit
5.0 out of 5 stars
1 review
Profile image

Great experience with Shaun. Despite short notice just before Christmas, he was available and was great about meeting our cat before we booked him. Would definitely use him again.

Availability updated 2 days ago
Sitter Profile Image: Nicole M.
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Sitter Profile Image: Nicole M.
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12. Nicole M.

Flexible schedule,
Millington, MD, 21651
14.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
11 reviews
3 repeat clients

Nicole is the most trustworthy pet caregiver we've ever had. She stayed in our home while we were out of town to take care of our 3 pets for an entire. She made sure our elderly pet received all of his medications and was generous with her love and comfort to our 3 pets. We've used other pet-sitters promised to take good care of our pets, but they all fell below expectations by only providing the bare minimum of care - food and water. We highly recommend Nicole!

Availability updated 11 days ago
Sitter Profile Image: Sabrina G.
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Sitter Profile Image: Sabrina G.
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13. Sabrina G.

Personalized Pet Care Specialist
Chestertown, MD, 21620
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per visit
4.4 out of 5 stars
23 reviews
6 repeat clients

Sabrina is a very conscientious dog owner. They have 3 dogs of their own that are all rescues. She has fostered problem dogs for a local rescue and taught them to behave so that they were adoptable.

Availability updated 10 days ago
Sitter Profile Image: Gillian H.
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Sitter Profile Image: Gillian H.
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14. Gillian H.

Animal lover
Chestertown, MD, 21620
0.1 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$14
per visit
4 reviews

"I can’t say enough wonderful things about Gillian as a pet sitter on Rover! She has taken care of my dog on multiple occasions, and each experience has been exceptional. Gillian is incredibly reliable, communicative, and clearly passionate about animals. From our first meeting, it was clear that she genuinely cared about making my pet feel safe and comfortable. Gillian kept me updated daily with messages and photos, which made me feel completely at ease while I was away. My dog absolutely adores her, and it's easy to see why—Gillian is attentive, playful, and goes above and beyond to make sure he has a great time. I could tell she followed all my care instructions closely and truly treated my pet like her own. If you're looking for a sitter who is dependable, kind, and experienced, I highly recommend Gillian. She has made every pet-sitting experience stress-free and enjoyable for both my pet and me!"

Availability updated 2 days ago
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Haley Z.
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Sitter Profile Image: Haley Z.
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15. Haley Z.

I can sit, walk, and run with pets!
chestertown, MD, 21678
10.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$13
per visit
5.0 out of 5 stars
4 reviews

I would highly recommend Haley to be a dog caregiver. As someone who has lived with her, I have seen how loving she is towards dogs, cats, and all animals. She is extremely passionate about animal life and does her best to advocate for their well-being. She cares deeply for animals (dogs included) and would be an extremely responsible dog caregiver.

Availability updated 33 days ago
Sitter Profile Image: Madison M.
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Sitter Profile Image: Madison M.
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16. Madison M.

I have dog fever and love pets
Millington, MD, 21651
9.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per visit
5.0 out of 5 stars
2 reviews

About: I currently own a Pitbull she’s now 3 and have had 3 other dogs in the past. I love all dogs big or small and am happy to give them the attention they need. If you have other pets in your home that is okay I have no allergies and am good with most other pets. Each pet is unique and may need extra care and I am more than okay with that. I am a nice, kind, and caring person and love animals with all my heart. I am great with specific schedules, being punctual, and love giving pets attention. I am here to make your life easier and help take care of your best friend(s). I work full time 8-5pm and I am free Saturdays. I always will be transparent about my schedule to be sure everything goes per expectation. I’m very respectful of your home and space. I want you to be able to go about your life and not be worried about your pets or anything on my end.

Availability updated 10 days ago
Sitter Profile Image: Joy P.
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Sitter Profile Image: Joy P.
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17. Joy P.

Can't imagine my life without a dog
Kennedyville, MD, 21645
8.9 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
1 review

About: I love dogs very much . Had them all of my life. I have 2 labs which are very spoiled. I would take very good care of your pet like it was my own. I am available on weekends or Friday and Saturday nights.Sunday during the day. I can come walk your dog during the day and evening on weekends and spend as much time with them as you like. I have a house with a fenced in yard out in the country. I have 2 acres. I would love too spend some time with your furry friends.I have been around animals all of my life. Can't imagine not having animals in my life. My dogs are always glad to see me when I get home and always put a smile on my face.

Availability updated over 1 year ago
Sitter Profile Image: Jack L.
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Sitter Profile Image: Jack L.
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18. Jack L.

Animal-lover wanting to help you!
Centreville, MD, 21617
10.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per visit
5.0 out of 5 stars
3 reviews

Jack has been taking care of our cats and dogs since early childhood. He is a kindhearted, caring and responsible young man who has a passion for animals. With almost a lifetime of experience, I would trust him to give any pet the love and respect they deserve.

Availability updated 14 days ago
Sitter Profile Image: Cindy C.
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Sitter Profile Image: Cindy C.
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19. Cindy C.

Paw-sitivity Sitter & Dog Mom of 2
Chestertown, MD, 21620
6.4 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
1 repeat client

About: Hi there! I'm Cindy, a devoted dog mom to two adorable pups who keep my life full of wagging tails and endless adventures. My love for animals knows no bounds, and I believe that every pet deserves to be treated with the same care and attention as my own furry family. Whether it’s a playful pup or a curious kitty, I’m here to ensure your pets feel loved, safe, and well cared for while you're away. After all, their happiness is my happiness! I provide attentive and reliable care in the comfort of your pet's own home, ensuring minimal disruption to their daily routine. Whether it's feeding, walks, playtime, or administering medication, I follow your instructions closely to keep your pets happy and healthy. Being a work-from-home professional allows me the flexibility to offer visits that fit seamlessly into your schedule, giving your pets the care and companionship they deserve throughout the day. Pet care is woven seamlessly into my daily routine. Since I work from home, I'm able to provide plenty of love and attention to my furry friends throughout the day. Whether it's a quick walk between meetings or some playtime to break up the workday, I’m always around to ensure your pets are happy and well cared for. When caring for pets in a client’s home, I treat their space with the utmost respect. I ensure that your pets feel comfortable in their familiar surroundings by maintaining their daily routines and offering lots of attention and care. Whether it’s feeding, walking, or just some extra cuddles, I make sure your pets are happy and content until you’re back.

Availability updated 57 days ago
Sitter Profile Image: Kashya J.
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Sitter Profile Image: Kashya J.
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20. Kashya J.

I love pets as much as I love kids
Chestertown, MD, 21620
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per visit
5.0 out of 5 stars
2 reviews
1 repeat client

About: Skillful pet caregiver for your fur baby. I’ve taken care of pets and have had a love for animals my entire life. Friends and family know that they can rely on me to love, socialize, walk, feed and bathe their pets. I work a very flexible schedule which allows me to have control of my schedule therefore I’m able to be super flexible with the hours that I choose to care for your pet(s). Pets are under my supervision at all times. If needed I’m also able to crate your pet as well. When going on walks all pets will be securely leashed.

Availability updated 6 months ago

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