Pet Sitting & Drop In Visits in Chilmark, MA

Book a pet sitter to stop by your home a few times a day to feed and play with your cat or dog.

1. Bailee

Walk? Run? Hike? Relax? Sure!

Westport, MA, 02790

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

1 repeat client

"So happy to have found this service to care for my dog and cat when I am away longer than they would like! From the moment Bailey arrived for her meet and gr... (more)"

Confirmed Memorial day Availability
2. Jacquelyn

Happy Tails on the Vineyard!

Vineyard Haven, Tisbury, MA, 02568

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

25 repeat clients

"It is possible that Jacquelyn is nicer to my dog and cat then I am......very reliable and very nice. This is our second experience and there will certainly b... (more)"

3. Savannah

Always around for your pet.

Mattapoisett, MA, 02739

House Sitting, Drop-In Visits

1 repeat client

"Thank you so much for the amazing care for my animals while I was away! I was recently on a 2 week vacation, leaving behind my two cats, my high energy pitbu... (more)"

4. Angela

Friendly Dog Lover on the Vineyard!

Vineyard Haven, MA, 02568

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: Living on Martha's Vineyard year round with flexible work schedule! I have had two dogs growing up, an energetic mix breed and a pug. I've have man... (more)

5. Hanny

I love being outdoors with dogs!

Falmouth, MA, 02540

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Hanny did a great job watching my dog, Maddie, when I was out of town for a week. She stayed at my apartment overnight with Maddie. Maddie had been having s... (more)"

6. Brian

Your at-home Veterinary Technician

oak bluffs, MA, 02557

House Sitting, Drop-In Visits, Dog Walking

About: Upbeat, experienced and professional animal nut, Island Spirit Kayak team member, with years of experience working primarily in small animal veteri... (more)

7. Leah

Walker, runner, hiker, biker

Chilmark, MA, 02535

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Leah was excellent - highly recommended! Prompt with replies, flexible, immediately comfortable with our pups, responsible and thorough. Our escape artist pu... (more)"

Confirmed Memorial day Availability
8. Shawn

Dogs love me... I love dogs

Buzzards Bay, MA, 02532

House Sitting, Drop-In Visits, Dog Walking

"Shawn loves animals - cats, dogs, goats... he has never come across an animal without wanting to be their best friend. He cares deeply about animals and the... (more)"

9. Corinne

Dog enthusiast; loyal & responsible

Marston Mills, MA, 02648

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Corinne has always loved and been committed to be around dogs. Regardless of breed, size, or personality, she has always had a connection and bond with her ... (more)"

10. Cassidy

Put your paws in good hands

Edgartown, MA, 02539

House Sitting, Drop-In Visits, Dog Walking

About: Been around dogs my whole life. Have mild training experience and just an overall love, appreciation, and understanding of all dogs. Comfortable wi... (more)

11. Amelia

Everything you want in a dog walker

Fairhaven, MA, 02719

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

About: Ive had dogs and cats my whole life. Big and small I love them all. Im not afraid to play in the mud, clean a pup or wash some poop off their feet!... (more)

12. Alyssa

ALWAYS have treats in my purse

Cotuit, MA, 02635

Drop-In Visits, Dog Walking

"She is a true pet lover. Especially dogs. She treats all the dogs in her life so speical. Her quiet nature is very comforting to dogs making her non threate... (more)"

13. Zachary

Reliable, honest, grew up with dogs

Dartmouth, MA, 02748

House Sitting, Drop-In Visits, Dog Walking

About: I have lived with dogs on a farm for all my life. I love animals and I have a special bond with dogs. I have cared for and trained 2 dogs from pup ... (more)

14. Emily

I’ll love your baby as much as you!

New Bedford, MA, 02740

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I am 28 years old and I've had dogs a majority of my life. I can't recall going more than 6 months without owning a dog. My dog is like family to ... (more)

15. Rachel

Lifelong and experienced dog lover

Edgartown, MA, 02539

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

1 repeat client

About: Hi! My name is Rachel and I recently moved back to the island for my sixth summer. Im currently only working part time and am eager to fill the res... (more)

16. Robin

Mature and dependable dog pal

New Bedford, MA, 02740

Drop-In Visits, Dog Walking

About: I know what you are looking for! A dependable, mature person who has your dog interests at heart. Being a former working professional, I know... (more)

17. Michael

Therapy dog, I enjoy the outdoors

Mashpee, MA, 02649

House Sitting, Drop-In Visits, Dog Walking

About: I am a loving,caring dog lover and I have a 9 year old chocolate lab who I raised to be a therapy dog. We attend children events who have disabilit... (more)

Confirmed Memorial day Availability
18. Abigail

Friendly Lifelong Animal Lover!

Centerville, MA, 02632

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"I can highly recommend Abby as a trusted pet caretaker. She had taken wonderful care of my schnauzer and two cats on numerous occasions, including several m... (more)"

19. Delayna

Furr Babyz Pet Care

Forestdale, MA, 02644

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

1 repeat client

"Delayna lover animals more than anyone I know.I trust her 100%, and she does a great job caring for my baby. If your looking for the right person for the job... (more)"

Confirmed Memorial day Availability
20. Paige

Semi Retired Registered Nurse

Sandwich, MA, 02563

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

"Paige is a seasoned pet owner. She is a very caring owner, and is a dedicated and loving caregiver. Paige would be a great addition to your Rover dog sitter ... (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 Chilmark 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 Chilmark, MA, 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 Chilmark pet sitters and avoid the kennel.