Pet Sitting & Drop In Visits in Chestertown, MD

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Alexandra

Trustworthy Animal Lover

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Allie was so accommodating for our last minute over night trip. We arranged for four (4) visits over a Saturday/Sunday overnight stay. She saved me from ca... (more)"

Confirmed Holiday Availability
2. Cassidy

Animal Lover wishin 2 love your Pet

Middle River, MD, 21220

House Sitting, Drop-In Visits, Dog Walking

About: I am a true animal lover and love dogs, cats, and other pets you may have equally. I raised my first puppy while I was in high school. He grew up... (more)

Confirmed Holiday Availability
3. Nora

Treat your dog like my own!

Catonsville , MD, 21228

House Sitting, Drop-In Visits

7 repeat clients

"Nora has been so helpful with the dogs and really flexible with her schedule. She's a lifesaver!! (more)"

4. Jessica

It's ok, my dogs my best friend too

Annapolis , MD, 21401

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

8 repeat clients

"My first time using Rover, and Jessica made it so simple to coordinate. She was great with my pup, and put my mind at ease. Thanks again! (more)"

Confirmed Holiday Availability
5. Elizabeth

Fur Ever Lover

Aberdeen, MD, 21001

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

2 repeat clients

"I have a 14 year old Bischon mix and a 17 year old Aussie. Liz is my first choice for dog care and I hire her for overnights because she is attentive, compa... (more)"

6. Britney

Vet Tech to care for your pets!

Baltimore, MD, 21220

Drop-In Visits

About: I have been a veterinary technician since 2005. I have two children, Rachael and Lucas. I live with my boyfriend whom I have been with since 2009. ... (more)

7. Becky

Enthusiastic and fun-loving

Annapolis, MD, 21401

House Sitting, Drop-In Visits

About: I have always had a special relationship with dogs. Never mattered the type, just that I got to enjoy their company. In my own life, I've been luck... (more)

8. Lauren

Fur baby lover

Annapolis , MD, 21401

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

"Lauren was a great sitter for my dog. My dog can be very anxious, but she was very calming with her and quickly became comfortable. Ever since the beginnin... (more)"

9. Karoline

Your "go to" when you need it

Greensboro, MD, 21639

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

About: I'm a stay at home wife who wants to be your "go to" when you need it. Although new to Rover, I'm not new to dogs and trying to understand them.... (more)

10. Kim

I ❤️animals

Sudlersville , MD, 21668

Drop-In Visits

About: I am 36 years old with two teenage boys. I am a stay-at-home mother. I have one dog one cat two birds lots of fish and tadpoles! I've had experienc... (more)

Confirmed Holiday Availability
11. Samantha

Experienced and loving pet sitter!

Canton, Baltimore , MD, 21231

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

"Samantha is Awesome!! She has taken wonderful care of my Bulldog (Zander) many times. Every time Zander see's her or hears her name he gets so excited :) you... (more)"

12. Tabatha

Great with all animals!

Whitemarsh, MD, 21162

Drop-In Visits

About: Hi, my name is Tabatha. I am 20years old and great with animals! I have been sitting animals since I was 14 years old and have had pretty much any ... (more)

13. Jake

I've had dogs my entire life!

Hamilton Area, Baltimore, MD, 21214

Drop-In Visits

"Jacob is perfect for sittings dogs, he has his own dog that he takes care of everyday this includes walking, feeding, cleaning up after, and washing his dog,... (more)"

Confirmed Holiday Availability
14. Melanie

10+ years of pet care experience

Glen arm, MD, 21057

House Sitting, Drop-In Visits, Dog Walking

About: I started assistant dog grooming/sitting/training at age 12 for a vet. From there I worked at a private dog groomers which also involved taking the... (more)

15. Katie

Animal lover available

Abingdon , MD, 21009

House Sitting, Drop-In Visits

"Katie is the best!! She has watched my five animals on numerous different occasions. I can always trust her to be timely and responsible with my babies. ... (more)"

16. Heather

Reliable & fun sitter available!

Abingdon, MD, 21009

Drop-In Visits, Dog Walking

"Heather did a great job taking care of my 8 year old American Bulldog and Pitbull mix named Rebel. She came to my home and stayed for a week, including over... (more)"

17. Rebekah

Reliable, caring, compassionate

Abingdon, MD, 21009

Drop-In Visits, Dog Walking

About: My name is Rebekah, I am 23 three years of age. I have been working with animals since the age of 18. I am a college graduate and I now own my own ... (more)

18. Corey

A True Dog Lover !

Cedonia, Baltimore, MD, 21206

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

About: A client should choose me to take of their dog because I have dogs of my own and I'm an inspiring to be a veterinarian and I been around dogs my wh... (more)

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Learn About Premier

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.