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.

1. Cheryl

Animal Lover with Huge Heart .

Belcamp, MD, 21017

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

"Cheryl Ryder Has Always loved her pets through the years I have known her and that's like 55 years now. She loves everything in life. She is very kind and t... (more)"

2. Kim

I ❤️animals

Sudlersville , MD, 21668

Drop-In Visits

1 repeat client

"Kim was absolutely wonderful! She did great with our hyperactive boxer dog. She is reliable and we greatly appreciate her help with drop in care. (more)"

3. Jennifer

Home full-time, great neighborhood!

Chestertown, MD, 21620

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

About: I am a 30 year old stay at home mom with two miniature dachshunds. They are super sweet and love other dogs and cats. I live in a house with a scre... (more)

4. Sarah

Energetic, responsible animal lover

Worton, MD, 21678

House Sitting, Drop-In Visits, Dog Walking

About: I have always loved animals, especially dogs, I have spent over 2000 community service hours helping with the Humane Society of Kent County MD's ad... (more)

5. Tracy

Home full time love for babies

Baltimore , MD, 21220

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

"Treated my dogs great. Left them for a weekend and came back to a couple of happy, healthy dogs. Definitely would recommend. Tell a friend! (more)"

6. Elizabeth

Furever friends!

Aberdeen, MD, 21001

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

4 repeat clients

"I own two cats who are both pretty finicky. One is extremely nervous around strangers but Liz won him over pretty quickly. She is patient and treats your ani... (more)"

7. Julianne

I'll walk/run/play with your dog!

Chestertown, MD, 21620

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

About: I have had dogs (and other pets) my entire life and I love helping them learn/grow. I grew up with a border collie and a chocolate lab. I current... (more)

8. Katelyn

I'll love your dog!

Dundalk, MD, 21222

Drop-In Visits, Dog Walking

1 repeat client

"Katelyn was so professional and friendly when I met her. She sent me a picture of my dog, Harper, while on their walk. I would definietly get Katelyn to walk... (more)"

9. Justine

Walk, Fetch, Groom, Relax

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Justine was great. Did exactly what I ask, showed up when promised and was great with my dog. Would highly recommend her! Brian H Stevensville MD (more)"

10. 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)

11. Elliot

Whatever your dog needs; I'll do

aberdeen, MD, 21001

House Sitting, Drop-In Visits, Dog Walking

"I am a certified Dog trainer and Dog nutritionist, I've worked with pets and their families almost all my life- for as long as I've known Elliot, if I wanted... (more)"

12. Jill

Dogs deserve love and lots of play

Riverside, Baltimore, MD, 21230

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

"Jill is such a friendly and enthusiastic person! I have been friends with Jill for six years now and have lived with her for a year. When we lived together w... (more)"

13. Kim

All animals love me

Church hill, MD, 21623

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

About: I love dogs I have 3 now they are my kids I love to play and walk with them.my dogs are my life they are my happiness .I like dogs more than must p... (more)

14. Brittney

I am home full-time

Aberdeen, MD, 21001

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

About: I used to have a dog and he passed while i was in Junior high school. His name was Bear and he loves to go on for a car ride, get ice cream, help m... (more)

Available this weekend
15. Kelly

Personalized attention for your dog

Sudlersville, MD, 21668

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

5 repeat clients

"Kelly is amazing with my two Boston Terriers! She's a reliable and kind professional who's also very flexible with last minute visits. Highly recommended. (more)"

16. Jake

I've had dogs my entire life!

Hamilton Area, Baltimore, MD, 21214

Drop-In Visits

"I've known Jake for a long time now and I can honestly say that he is one of the easy-going people I know. He can get along with practically anyone, and have... (more)"

17. 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)"

18. 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)"

19. Kate

Dog Lover Who Will Spoil Your Dog!

Stevensville, MD, 21666

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

"My name is Alex, and Kate pet sat for my wife and I while we were out of town. We had a meeting ahead of time so our dog could get to know her and they seeme... (more)"

20. Lauren

Fur baby lover

Annapolis , MD, 21401

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

2 repeat clients

About: I'm 30 and recently just moved to Annapolis. I've grown up with all different kinds of animals, dogs, rabbits, hermit crabs, and a giant iguana! I'... (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.