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. 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)"

2. Lorel

Flexible, reliable dog lover

Aberdeen, MD, 21001

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

1 repeat client

"Lorel was very kind and gentle with Gracie. It takes awhile for Gracie to warm up to people but by the time Lorel left...they were friends. Scheduled another... (more)"

3. 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)"

4. 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)"

5. 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)"

6. Jene'

Doggies Galore

Abingdon, MD, 21009

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

About: I worked at a Doggie Day Care and a Vet Hospital for over 5 years. I am Pet Care Safety Certified, First Aid and CPR Certified and, I am also a Vet... (more)

7. Jennifer

I'm a huge dog lover and reliable.

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Jennifer did drop in visits with and my pups. They loved her. She came to meet our dogs before our trip and asked a lot of great questions. She reached out... (more)"

8. Elizabeth

Furever friends!

Aberdeen, MD, 21001

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

10 repeat clients

"Over the past several years Elizabeth Garcia has assisted me in the care and grooming of my animals. Elizabeth seems to have a special way of communicating ... (more)"

9. Julia

We'll go on long adventurous walks!

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

"Julia is a very responsible person who has much experience in dog handling. Having dealt with dogs her entire life, she knows the difference in walking a sma... (more)"

10. Melanie

Lover of all 4-legged things :)

Middle River, MD, 21220

Drop-In Visits, Dog Walking

1 repeat client

"Melanie was fantastic, we are often concerned when leaving out "FurSon" in the care of others to travel. Melanie took all the worrying away, we received Pict... (more)"

11. 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

"I've worked with Neal the last few years and found him to be a hard and open worker. He will ensure the safety and comfort of your pets and ask questions whe... (more)"

12. Sarah

Who doesn't want a dog's love?

Edgewood, MD, 21040

House Sitting, Drop-In Visits, Dog Walking

About: What dog owners will appreciate about the care i provide is my excitement for dogs, heart of love, hard work, and experience of taking care of the... (more)

13. 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)

14. Cierra

Vet tech with 10 yrs+ experience

Baltimore, MD, 21221

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

"Cierra is a very kind and understanding person with both people and animals. She has more than enough experience dealing with all kinds of dogs of all differ... (more)"

15. 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)"

16. 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)

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. 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)"

19. Aaliyah

I love animals so much!

Essex, MD, 21221

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

"I have to say that Aaliyah is a wonderful person to have watch your dogs. She is loving, caring, and willing to always have fun. Treats are a thing she loves... (more)"

20. 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)


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.