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.

Tip: Contact sitters now to confirm availability.
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1. Jacquelyn

Happy Tails on the Vineyard!

Vineyard Haven, Tisbury, MA, 02568

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

"Jacquelyn was fantastic with our 2 dogs! When she came over to meet them for the first time, they were very excited to see her, they could sense she is a rea... (more)"

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2. Bailee

Walk? Run? Hike? Relax? Sure!

Westport, MA, 02790

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

"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)"

3. Bridget

Dogs love me as much as I love them

Mattapoisett, MA, 02739

House Sitting, Drop-In Visits, Dog Walking

About: I’ve owned my Australian Labradoodle, Tuukka, for 4 years and have raised him since he was a puppy. I’m experienced in training puppies and dogs, a... (more)

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4. Savannah

Always around for your pet.

Mattapoisett, MA, 02739

House Sitting, Drop-In Visits

"Savannah is an incredibly kind and caring person who adores fluffers of all kinds! She is responsible and patient and will provide lots of love to your babie... (more)"

5. 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)

6. Hanny

I love being outdoors with dogs!

Falmouth, MA, 02540

House Sitting, Drop-In Visits, Dog Walking

"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)"

Confirmed availability
4th of July
7. Faith

Let me take your dog to the beach!

Aquinnah, MA, 02535

House Sitting, Drop-In Visits, Dog Walking

"Faith is not only the best dog sitter but she is a dog entertainer.. she keeps my pup on the go.. she loves and cares for pets that are not even hers… She h... (more)"

8. Leah

Walker, runner, hiker, biker

Chilmark, MA, 02535

House Sitting, Drop-In Visits

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

9. 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)

10. Emily

I’ll love your baby as much as you!

New Bedford, MA, 02740

House Sitting, Drop-In Visits, Dog Walking

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)

Confirmed availability
This weekend
11. 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)

12. 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)

Confirmed availability
This weekend
13. Anna

Me&dogs have that special connectio

NEW BEDFORD, MA, 02744

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

"I’ve known Anna for 7 years. She is a really good friend and a kind person. She is in love with all the animals. Anna use to be a dog sitter a couple years ... (more)"

14. Corinne

Dog enthusiast; loyal & responsible

Marston Mills, MA, 02648

House Sitting, Drop-In Visits, Dog Walking

"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)"

15. Ashley E.

Avid Dog Rescuer and Animal Lover

Oak Bluffs, MA, 02557

House Sitting, Drop-In Visits, Dog Walking

"Ashley has been my best choice for pet care.. She is very easy to communicate with and our dogs love her.. She keeps us updated and always sends us photos of... (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)

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18. Michaela

Fun-loving, dependable dog lover

New Bedford, MA, 02745

Drop-In Visits, Dog Walking

About: My name is Michaela and I've always been an animal lover. I have gotten most of my experience from caring for all of my own animals. I currently ha... (more)

19. Schuyler

Animal lover, big or small.

West Tisbury, MA, 02575

House Sitting, Drop-In Visits, Dog Walking

"Schuyler has a lifelong love of animals, but maybe even more important, she has an extraordinary ability to understand their needs and personalities, and to ... (more)"

20. Gigi

I will treat your pup like my own

Edgartown, MA, 02539

Drop-In Visits, Dog Walking

"I have never met or even seen someone who loves dogs more than Gigi. We can't even have a conversation walking down the street without her completely forgett... (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.