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. 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. Douglas

Compassionate with flexible hours!

Chestertown, Maryland, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

"Well it's not like Douglas needs my Testimonial to be qualified to be a Rover Dog Caregiver the fact is that Rover needs Douglas because he is the most Lovin... (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. 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)

5. Maddie

pups, dogs, and elders!

Worton, MD, 21678

Drop-In Visits, Dog Walking

2 repeat clients

"1st time using Rover... Maddie took great care of our pup during her visit. She was able to do everything we asked of her and based on the pictures we receiv... (more)"

6. Julia

We'll go on long adventurous walks!

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Julia was extremely professional and polite. She thoroughly communicated with me the entire time I was away and took well care of Gideon (my dog). I know he ... (more)"

7. Cierra

My love for animals is unbelievable

Middle River, MD, 21220

House Sitting, Drop-In Visits, Dog Walking

About: I've 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 th... (more)

8. 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)"

9. Amber

Active, loving and caring

Millington, MD, 21651

House Sitting, Drop-In Visits, Dog Walking

"I have know Amber for ten years and for as long as I've known her she has always been obsessed with animals. She loves her dogs and I know she would do an am... (more)"

10. Callie

Live, Love, Bark!

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

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

"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)"

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. 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)"

14. 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)"

15. 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)"

16. 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)"

17. 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)"

18. Rachel

Professional Experience with AWL

Stevensville, MD, 21666

House Sitting, Drop-In Visits

"if you're looking for someone to love and watch over your pets while you're away, it's definitely Rachel! She has a HUGE heart for animals. She has taken gr... (more)"

19. Jena

Experienced Pet Sitter 4+ Years

Grasonville, MD, 21638

Drop-In Visits, Dog Walking

About: My name is Jena, not only have I had pets of my own since I was little, but I have also owned a pet and house sitting business for the past 4 years... (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.