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.

Confirmed Holiday Availability
1. Jacquelyn

Happy Tails on the Vineyard!

Vineyard Haven, Tisbury, MA, 02568

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

21 repeat clients

"Jacquelyn took care of our dog Maddie with love and care and it was very much appreciated. We will certainly use this service again. Thank you so much! Deb... (more)"

Confirmed Holiday Availability
2. Guinnevere

Your Dog's Best Friend

Assonet, MA, 02702

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Guinevere has been watching my 3 dogs since 2010. I can't imagine anyone else to trust them with. I even have her now travel to NC to watch my dogs while I t... (more)"

3. Hanny

I love being outdoors with dogs!

Falmouth, MA, 02540

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I have two rambunctious dogs that can be difficult to take care of. Hanny is loving, patient yet firm when necessary. She was a wonderful sitter, spending a ... (more)"

4. Katherine

Personalized love-flexible schedule

edgartown, MA, 02539

Dog Boarding, Drop-In Visits, Dog Walking

"I have known Kat her entire life. She has always been an animal person, having cared for a wide array of critters, from guinea pigs, to horses, to dogs and ... (more)"

5. 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)

6. Angela

Friendly Dog Lover on the Vineyard!

Vineyard Haven, MA, 02568

House Sitting, Drop-In Visits, Dog Walking

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)

7. 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)"

8. Joshua

Premier Pet Sitting

Narragansett, RI, 02882

Drop-In Visits

"I've known Joshua for nearly 12 years, and I've been using his services as a pet sitter for nearly 10 years. It's not easy watching the pets in my househo... (more)"

Confirmed Holiday Availability
9. Alisia

Loving your dogs as much as you!

New Bedford, MA, 02745

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

1 repeat client

"Alisia is an amazing person who puts animals over before her own self and makes any dog feel like they are part of the family. She has been taking care of an... (more)"

10. 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)"

Confirmed Holiday Availability
11. Katelyn

5 year professional animal care

East falmouth, MA, 02536

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

About: I have been working for a professional animal care Company for over five years now, I am also a groomer. Animals are my passion and I take my job... (more)

12. Julia

Taking the best care of your pet

East Greenwich, RI, 02818

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

About: Having a German Shepherd for years and currently the proud mom of a Husky, I know what it takes to deal with all type of dogs whether big or small.... (more)

Confirmed Holiday Availability
13. Maria

Paws First

Centerville, MA, 02632

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

About: I have worked in multiple shelters and doggy day cares/boarding facilities in my twenty years. I was a Senior Kennel Tech in the most recent Doggy ... (more)

14. 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)

Confirmed Holiday Availability
15. Summer

Experience in dog shelters

West barnstable, MA, 02668

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

"Summer is not only an amazing people person but is excellent with animals. Summer is loving, caring and nurturing when it comes to the well being of an anima... (more)"

Confirmed Christmas Availability
16. 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)"

Confirmed Holiday Availability
17. Rosemary

I'm an outgoing, animal lover!

Tiverton, RI, 02878

House Sitting, Drop-In Visits, Dog Walking

"Rosemary is a great help and my 2 year old dog loves her! She walked my dog about three times a week when I worked long hours. Mickey (my dog) loves his walk... (more)"

18. Amy

Good chance I'll cry tears of joy

Tiverton, RI, 02878

House Sitting, Drop-In Visits, Dog Walking

About: If you don't cry when you see a puppy, we can't be friends. I have had dog-sitting and house-sitting experience with the same family on two separat... (more)

Confirmed Holiday Availability
19. Delayna

Furr Babyz Pet Care

Forestdale, MA, 02644

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 Holiday Availability
20. Paige

Semi Retired Registered Nurse

Sandwich, MA, 02563

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.