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.

Tip: Contact sitters now to confirm availability.
Confirmed availability
4th of July
1. Ashley

Endless cuddles for your fur baby

Edgewood, MD, 21040

House Sitting, Drop-In Visits, Dog Walking

"Ashley has been a great petsitter for many dogs and cats for a long time. She is very responsible and trustworthy. She loves her own dogs like they are her c... (more)"

2. Kim

I ❤️animals

Sudlersville , MD, 21668

Drop-In Visits

"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. 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)"

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4. Allison

Part-Time, Flexible Hrs, Adore Dogs

Baltimore, MD, 21220

House Sitting, Drop-In Visits, Dog Walking

About: Let’s be honest, dogs are truly our best friends! I have grown-up and have been taking care of/surrounded by dogs my entire life. I currently am su... (more)

5. Meghan

Animal-Loving Teacher ???

Sparrows Point, MD, 21219

House Sitting, Drop-In Visits

"Meghan has watched our cats and really treats them like her own. She is very reliable and will go above and beyond when watching your pet. We have 2 very ne... (more)"

Confirmed availability
4th of July
6. 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)"

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7. 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)"

Confirmed availability
4th of July
8. Jennifer

Home full-time, great neighborhood!

Chestertown, MD, 21620

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

"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 availability
4th of July
9. Harmony

Doggy runs and walks!

Edgewood, MD, 21040

Drop-In Visits, Dog Walking

"Harmony is the best! She is dependable, punctual and absolutely LOVES our two cats and dog. She left daily notes for us to see that she was there and wha... (more)"

10. Neal

Dog love to run/hike? Perfect!

Stevensville, MD, 21666

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

"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)"

11. 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)

12. Audreanna

Home full time, fenced in yard

Centreville, MD, 21617

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

About: I am basically a stay at home mom. I work one day a week at a dog grooming salon, I am a pet stylist! I have always loved working with dogs and I s... (more)

13. Norah

Energetic and ready for your dogs

Stevensville, MD, 21666

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

"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)"

14. Rebekah

Wide open schedule- love animals

Marydel, DE, 19964

Drop-In Visits, Dog Walking

"On time, did what was asked and got along great with my Bailey. Would recommend Rebekah to everyone. Will book again soon!! (more)"

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15. Annie

I love all doggies!!

Centreville, MD, 21617

House Sitting, Drop-In Visits, Dog Walking

"Annie is very caring and loves dogs so much, she is great when playing and walking them as well! I would recommend this hardworking girl to anyone. (more)"

16. 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)

Confirmed availability
4th of July
17. 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)"

Confirmed availability
4th of July
18. Siara

Home full-time, boarding offered!

Middle River, MD, 21220

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

"Siara is reliable and available with a flexible schedule. She's always willing to pick up another client whether it's dog-walking or baby-sitting, and we kno... (more)"

19. Cierra

Vet tech with 10 yrs+ experience

Baltimore, MD, 21221

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

"Cierra is awesome with animals. She is very loving , attentive. She is very reliable and dependable if I needed Sitter I would call on her . She is reliable ... (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.

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.