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. Madison

Friendly petsitter

Aberdeen, MD, 21001

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

2 repeat clients

"She is so great with dogs. my three pit bulls loved her when she came in my house for first time 7 years ago. (Normally, my family pit bulls don't like stran... (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

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)"

4. 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)"

Available this weekend
5. Norah

Energetic and ready for your dogs

Stevensville, MD, 21666

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

"I have known Norah for many years and found her to be a hard and open worker. She will ensure the safety and comfort of your pets and ask questions when need... (more)"

6. Elizabeth

Furever friends!

Aberdeen, MD, 21001

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

6 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)"

7. 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)"

8. 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)

9. Jennifer

I'm a huge dog lover and reliable.

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"This was my first time using Jen or anyone on Rover. She did a drop in visit. She texted me with updates, which was a relief. She made me comfortable in kno... (more)"

10. Rachel

Professional Experience with AWL

Grasonville, MD, 21638

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)"

11. Amanda

Love those Fur-Babies!

Baltimore, MD, 21221

House Sitting, Drop-In Visits, Dog Walking

About: Hi I'm Amanda! I'm a HR professional in Baltimore and life-long dog lover. Large or small, any age, I love them all! I grew up in a dog (and cat... (more)

12. 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)

13. 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)"

14. 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)"

15. 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)

16. 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)

17. 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)"

18. 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)

19. 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)

20. 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)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

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.