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.

Confirmed Holiday Availability
1. 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)"

2. Callie

Live, Love, Bark!

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

"Usually I am skeptical about leaving Sasha, my two year old husky with a sitter due to her separation anxiety(on top of her off-the-chain energy levels) but ... (more)"

3. Mark

Exp. vet assistant and kennel help

Aberdeen, MD, 21001

House Sitting, Drop-In Visits

"Mark stayed at my house for a week and a half while I was away for my wedding. My mom's dog was also staying there with Mark. So, in total, he had 4 dogs a... (more)"

4. Jesse

Dog Lover Sits in YOUR Home

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"I have known Jesse since he was a teen. He has always been a very caring, gentle guy especially when it comes to animals. His family has had dogs for years... (more)"

Confirmed Holiday Availability
5. Rachel

Professional Experience with AWL

Stevensville, MD, 21666

House Sitting, Drop-In Visits

"I have known Rachel for her whole life. She is very sweet, honest and reliable. She loves animals like no-one I know. She would be a great asset to have work... (more)"

6. Katelyn

I'll love your dog!

Dundalk, MD, 21222

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Katelyn was consistent with early arrival to take our pup out daily! She was caring and respectful of our house and kept us updated constantly! (more)"

Confirmed Holiday Availability
7. Jennifer

Home full-time, great neighborhood!

Chestertown, MD, 21620

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

1 repeat client

"We are new to the area, and Jenn recently took my Very large Newfie for a walk after doing a meet and greet with her. She left me a note afterward and prompt... (more)"

Confirmed Holiday Availability
8. Olivia

Experienced and active dog lover

Belcamp, MD, 21017

House Sitting, Drop-In Visits, Dog Walking

About: I have cared for dogs for my entire life and am an experienced pet sitter for cats, dogs, and fish. I currently have a pit/lab mix and a lab/hound ... (more)

9. Aaliyah

I love animals so much!

Essex, MD, 21221

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

"Aaliyah has watched my dog on many occasions and it’s been a great experience, haven’t had any problems! She is friendly and her dog is very playful and happy. (more)"

10. Neal

Dog love to run/hike? Perfect!

Stevensville, MD, 21666

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

1 repeat client

"He is very responsible, and love to have animals around him. He love to take dogs to trail. Also he always keep house clean. Neal is fun person. fun facts ab... (more)"

Confirmed Holiday Availability
11. Madison

Dependable Doggie Sitter/Walker :-)

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Madison is just AMAZING!! She takes my Weimaraner on long walks and even treats him to fetching the stick into the river and giving him a bath!! Madison is v... (more)"

12. 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)"

Confirmed Holiday Availability
13. Elizabeth

Furever friends!

Aberdeen, MD, 21001

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

6 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)"

14. Jennifer

I'm a huge dog lover and reliable.

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Everything went great. Jennifer showed up on time and left several pictures each time, which I loved. She exercised my pups and they were happy campers. W... (more)"

15. Katie

Animal lover available

Abingdon , MD, 21009

Drop-In Visits

"Katie is a responsible mother who takes great care of animals! I employed her to take care of my dog while I was out of town on business. Not only did she te... (more)"

Confirmed Holiday Availability
16. Norah

Energetic and ready for your dogs

Stevensville, MD, 21666

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

1 repeat client

"NorH took care of my pugs without any problems. We are happy to have found her and appreciate her last minute help to have carefor the pups. (more)"

17. Angela

Dogs are family

Clayton, DE, 19938

House Sitting, Drop-In Visits, Dog Walking

About: All dogs love me and I love them. I like to get down on the floor and play with them and take them for walks and throw the ball around for them to ... (more)

18. Kimberly

Kim's dog walking and house sitting

Marydel, DE, 19964

House Sitting, Drop-In Visits, Dog Walking

About: I have always had pets in my home for most of my life. I have mostly had dogs and cats, I also have had ferrets and helped family care for 2 parro... (more)

19. Cierra

My love for animals is unbelievable

Middle River, MD, 21220

House Sitting, Drop-In Visits, Dog Walking

About: Ive had dogs my whole life since I can remember. I started dog walking and dog sitting at about the age of 10. Started with family and then did the... (more)

20. 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)


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.