Pet Sitting in Chester

Book a pet sitter to stop by your home a few times a day to feed and play with your cat or dog.

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1. Rachel Verified Background CheckRover 101

Bet I can make your dog’s tail wag!

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

"Rachel is just the type of fur-sitter I was hoping for! She has great communication and truly loves and cares for Sonny during the drop-in visits as her own! D… (more)"

2. Jamie Verified Background Check

Best Buddy for the Furry Royalty

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"She is so kind and actually spends time with my bunnies! She does everything she is asked and even stays to play with them! I am so happy to have Jamie as a si… (more)"

Confirmed availability
 Easter weekend
3. Ginger Verified Enhanced Background Check

Stevensville, Chester, Grasonville

Kent Island, Bay Bridge Cove, Stevensville, MD, 21666

Drop-In Visits, Dog Walking

"Always reliable and takes great care of my pup! 10/10 recommend! (more)"

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4. Kate Verified Enhanced Background Check

Here for you, rain or shine!

Annapolis, MD, 21401

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"If I could give a 10 Star review, I would!! She is absolutely amazing and I highly recommend her to watch over your fur babies in the future! Kate, you are t… (more)"

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5. Michaila Verified Background Check

I’m happy to meet new furry friends

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

"Michaila has always been very trustworthy and responsible with animals. She works very well with them and seems to have a special relationship with each animal… (more)"

Confirmed availability
 Easter weekend
6. Dominic Verified Background Check

I love and am good with pets!

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Dominic is a very dependable dog walker. He always arrives on time. Our dog is very happy to go out with him. We highly recommend him. (more)"

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7. Emily Verified Background Check

Will love a dog as if its my own!

Annapolis, MD, 21409

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

"Emily recently watched our cat for a long weekend. She was an excellent sitter who was prompt, professional, sweet, and flexible! She sent many pictures while … (more)"

8. Kasey Verified Background Check

All breeds welcomed and loved

Stevensville, MD, 21666

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Definitely will be having Kasey let out my pup again! She kept me updated on his visit! Thank you! (more)"

Confirmed availability
 Easter weekend
9. Ashley Marie Verified Background CheckRover 101

Stay at home Mom and animal lover!

Annapolis, MD, 21409

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"My family went to Europe and I was concerned about the care of my cat while being out of the country. Ashley put my mind at ease. She amazed me with how quick… (more)"

Confirmed availability
 Easter weekend
10. Bohdanna Verified Background CheckRover 101

I Love Furbabies!

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

"Bo was very professional and I could immediately that she is an animal lover. Otis was happy for his midday walk and ball time. I will def be using her again. (more)"

Confirmed availability
 Easter weekend
11. Megan Verified Background CheckRover 101

Loving your pets as my own!

Annapolis, MD, 21402

Dog Boarding, Drop-In Visits, Dog Walking

"Easy to work with. Very caring of my pet. Will use again! (more)"

12. Jen Verified Enhanced Background Check

Life-long animal lover!

Annapolis, MD, 21409

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Jen took care of my 3 cats for a weekend and did a wonderful job! She was timely and kept in communication with me. She sent picture updates at each visit, whi… (more)"

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13. Jason & Tracy Verified Enhanced Background CheckRover 101

Reliable & Responsible, Dog Lovers!

Stevensville, MD, 21666

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"We love Jason! Can always count on him. Five days and nights Jason stayed, cared for and walked 2 Dobermans. Jason is the Dog Whisper. Thank you for being… (more)"

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14. Melanie Verified Enhanced Background Check

Animals are my spirit animal(s)!

Grasonville, MD, 21638

Drop-In Visits, Dog Walking

About: Chances are, I like your pets more than I like you! Just kidding! But in all seriousness, they are the best. Nothing heals a bad day like a tail w… (more)

15. Kaitlin Verified Background Check

All love and experience for pets!

Grasonville, MD, 21638

Drop-In Visits, Dog Walking

"She is wonderful with Savannah. Gives her lots of love and attention. (more)"

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16. Katelyn Verified Background Check

An experienced dog owner

Chester, MD, 21619

Dog Boarding, Drop-In Visits, Dog Walking

"Kate was (is!) great! Took great care of Yo-Yo, easy to contact, and super friendly - I think Yo-Yo was upset we had to come home! Thanks, Kate! (more)"

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17. Madeline Verified Background Check

Excited to Help Out!

Chester, MD, 21619

House Sitting, Drop-In Visits, Dog Walking

"Maddie has provided amazing and compassionate care to our animals. Her kindness and gentleness with animals is readily apparent in her nature from the time you… (more)"

18. Kaitlin Verified Background Check

ER Vet Tech w/ Pet Sitting Exp

Stevensville, MD, 21666

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Kaitlin was amazing. She allowed me to book in a moments notice, and kept me informed the entire time. I know my fur babies were in excellent hands! Will defin… (more)"

Confirmed availability
 Easter weekend
19. Pamela Verified Background Check

Honest, gentle and friendly

Grasonville, MD, 21638

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Pam is the best! She goes above and beyond to make sure our pups are happy and taken care of. (more)"

Confirmed availability
 Easter weekend
20. Alexis Verified Background Check

Reliable, loving and responsible!

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

About: Hi! What I can offer for you and your pet is amazing in home care. Daily walks and feedings and of course cuddles! I can bathe and clip nails. I can … (more)


As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Chester pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Chester, MD who meets your — and your pet's — needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet — including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.