Pet Sitting in Chestertown

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

Confirmed availability
 Easter weekend
1. Elizabeth Verified Enhanced Background CheckRover 101

How do you spell love? D-O-G!

Abingdon, MD, 21009

House Sitting, Drop-In Visits, Dog Walking

"Lizz did an amazing job checking up on our 2 cats while we were on vacation. It was so nice coming home to see how happy and well taken care of they were. I wi… (more)"

2. Kelly Verified Enhanced Background Check

Coonhound Mom &Dog Auntie for Hire

Middle river, MD, 21220

Drop-In Visits, Dog Walking

"My dogs love it when “Aunt Kelly” comes to visit. They get plenty of outside time and exercise. She is great to communicate with and reliable. She’s happy to c… (more)"

Confirmed availability
 Easter weekend
3. Tanya Verified Background Check

Your pet will be treated with care

Edgewood, MD, 21040

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

"Tanya was awesome! She was accommodating to all of my requests and kept me updated about her visits with my cats. Would recommend! (more)"

4. Elizabeth Verified Background Check

Furever friends!

Aberdeen., MD, 21001

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

"We have a German Sheppard, and we are precautions with new people meeting her but Elizabeth did amazing! Our dog immediately liked Elizabeth and started playin… (more)"

Confirmed availability
 Easter weekend
5. Kirstie Verified Background CheckRover 101

We make it feel just like home!

Middle River, MD, 21220

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

About: Hi all! Welcome to our Doggy Vacay page! We are so happy you're thinking about watching your fur babies. Just a few notes about us below. We love … (more)

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6. Nicole Verified Background Check

Weekend Dog Walker

White Marsh, MD, 21162

Drop-In Visits, Dog Walking

"Nicole was great! She dropped in and walked my lab while i was out of town for the night and sent adorable pictures from their walk. (more)"

Confirmed availability
 Easter weekend
7. Brittany Verified Background CheckRover 101

Cat, Dog, Fish, other- I can do it!

Abingdon, MD, 21009

House Sitting, Drop-In Visits, Dog Walking

"Brittany was the first sitter to get back to me, since Rover recommends contacting multiple people! That is really important to me that she was so responsive… (more)"

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8. Rachel Verified Background Check

Experienced and reliable pet sitter

Centreville, MD, 21617

House Sitting, Drop-In Visits, Dog Walking

"Rachel was great, I contacted her last minute about watching my cat and she responded right away. We will definitely use her again for cat sitting or dog walks! (more)"

9. Breeanna Verified Background Check

Fur Babies For Life

Centreville, MD, 21617

Drop-In Visits

About: Hello fur moms and dads! My name is Breeanna, but you may call me Bree. My love for animals has come a long way. I've had cats, dogs, a mouse, and ha… (more)

Confirmed availability
 Easter weekend
10. Ashley Verified Background Check

Animal loving college student

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

"Ashley is a mature responsible young adult with very strong arms. She can walk the most unruly dog and he’s like a puppy with her. All animals seem to go to he… (more)"

11. Agnes Verified Background Check

super flexible schedule

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

"Agnes was available to do a drop in visit on short notice. She is friendly, personable and clearly a dog lover. She followed our instructions to the letter inc… (more)"

12. Jeren Verified Background Check

Stay at home mom and animal lover

Centreville, MD, 21617

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

"Jeren did a wonderful job of taking care of my 2 cats for 2 weeks while I was out of the country. She sent me daily updates and pictures. I highly recommend h… (more)"

13. Joy Verified Background Check

Can't imagine my life without a dog

Kennedyville, MD, 21645

Dog Boarding, Drop-In Visits, Dog Walking

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 … (more)

14. Katelynn Verified Background Check

I’ll treat your pets as my own!

centrevillle, MD, 21617

House Sitting, Drop-In Visits, Dog Walking

About: Hi! My name is Katelynn and I love animals; dogs especially. I am 18, and attend a local community college. I would be delighted to watch/walk your d… (more)

15. maddi Verified Background Check

I can’t wait to meet you & ur pet!

Centreville, MD, 21617

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

About: Hi! I’m Madelynn Richards and I’m a senior in high school! I’ve always had some kind of pet in my home and have always had a special place in my hear… (more)

16. Breanna Verified Background Check

Animals make the world go ‘round

Chestertown, MD, 21620

Drop-In Visits, Dog Walking

About: I’m a very honest and reliable person! It’s important to me to be the very best I can be for the owner and their companions! I love going on walks an… (more)

17. Bess Verified Background Check

I love the outdoors and dogs

Chestertown, MD, 21620

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

"Bess has watched and walked my neighbors dog, and was so good to him. She was by far the best dog sitter they had ever had. (more)"

18. Lexie Verified Background Check

Loving Dog Walker/Sitter

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

"Lexie W. is a dog lover in the truest sense. She loves her 2 dogs like they are her kids. She has volunteered at the local animal rescue so she has been resp… (more)"

19. Dani Verified Enhanced Background Check

Pawsitively the Best

Centreville, MD, 21617

House Sitting, Drop-In Visits, Dog Walking

About: I care for our Yorkshire Terrier (Finnley) who we rescued from a rescue in New York City five years ago. I love pets and enjoy pet sitting, taking wa… (more)

20. Cynthia Verified Background Check

They are family not pets.

Rock Hall, MD, 21661

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

About: I have been born and raised to take care of any type of family member from the small lizard to largest dog to feathered friends and horses. I love al… (more)


The next time you head out of town and need someone to take care of your pets — and check in on you home — turn to Rover. It's easy to find a loving Chestertown pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Chestertown, MD, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover — it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Chestertown pet sitters and avoid the kennel.