Pet Sitting & Drop In Visits in Chester, 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. Tammy

Dog loving family

Westfield, MA, 01085

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

3 repeat clients

"I was very happy with taking care of my Dachys while we were away (more)"

2. Taylor

The animals always come first.

Granville , MA, 01034

House Sitting, Drop-In Visits, Dog Walking

"Taylor is a very smart and caring woman who loves caring for all types of pets. She has a sweet disposition and has a lot of experience that allows her to ca... (more)"

3. Melissa

Melissa lives at end of a dirt rd.

Russell, MA, 01071

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

"It is my pleasure to recommend Melissa as a caregiver for your furry family member/s. Her care and consideration for an animals individuality and needs is ex... (more)"

4. Luke

3/5 barn builder, 2/5 dog walker

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

About: Hey! I'm Luke! I've cared for dogs all my life. My dog now, Chai Chai, is a sassy princess but we all still love her. Honestly, I can't have enough... (more)

5. Michael

Friendly guy, to both people & dogs

Florence, MA, 01062

House Sitting, Drop-In Visits, Dog Walking

"Such is Michael's love for pups that that is what I call him - Pup! Pup speaks often and lovingly of the pup of his youth, Kasha, a handsome Samoyed with reg... (more)"

6. Kayla

I would love to help!!

Huntington, MA, 01050

House Sitting, Drop-In Visits, Dog Walking

About: I've grown up around dogs my whole life and have always had a love for them. They have taught me love and responsibility. I also have a horse of my... (more)

7. Victoria

I go above and beyond, every time.

Westfield, MA, 01085

House Sitting, Drop-In Visits, Dog Walking

About: For over 8 years, I have cared for all ages, sizes, breeds, and temperaments of dogs. Keeping your pet happy, healthy, comfortable, exercised, fed,... (more)

8. Molly

Responsible and caring

Granby , CT, 06035

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I am so happy to write a testimonial for Molly H. We have a 14 year old Italian Greyhound who is as dear to us as our 2 legged children. Denali has never b... (more)"

9. Erika

social worker and dog lover

Westfield, MA, 01085

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

About: I particularly do not have any history taking care of dogs, but I have grown up with puppies and older dogs as a child through my adulthood. I have... (more)

10. Alexandra

Flexible hours, own a dog

Northampton, MA, 01060

House Sitting, Dog Walking

4 repeat clients

"We had Lexa come stay at our place to watch our dog for 3 nights. She sent a bunch of photos and updates which was great and kept our minds at ease the whole... (more)"

11. Melissa

Melissa lives at end of a dirt rd.

Russell, MA, 01071

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

"Great dog sitter! Melissa cared for our dog in her home for nearly two weeks and we were very pleased with the attention and care that she provided. She has ... (more)"

12. Taylor

The animals always come first.

Granville , MA, 01034

House Sitting, Drop-In Visits, Dog Walking

"Taylor is dependable and quick to respond at any text or call. I feel fortunate to have found her and you can feel confident in hiring her. She came to my ho... (more)"

13. Michael

Friendly guy, to both people & dogs

Florence, MA, 01062

House Sitting, Drop-In Visits, Dog Walking

"Such is Michael's love for pups that that is what I call him - Pup! Pup speaks often and lovingly of the pup of his youth, Kasha, a handsome Samoyed with reg... (more)"

14. Molly

Responsible and caring

Granby , CT, 06035

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I am so happy to write a testimonial for Molly H. We have a 14 year old Italian Greyhound who is as dear to us as our 2 legged children. Denali has never b... (more)"

15. Luke

3/5 barn builder, 2/5 dog walker

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

About: Hey! I'm Luke! I've cared for dogs all my life. My dog now, Chai Chai, is a sassy princess but we all still love her. Honestly, I can't have enough... (more)

16. Mallory

Experienced Pet Sitter at Your Service!

Amherst, MA, 01003

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"This is the second time we have had Mallory watch Lucy, She is reliable, takes Lucy on great adventures, sends photos and updates and Lucy really likes her. ... (more)"

17. Kayla

I would love to help!!

Huntington, MA, 01050

House Sitting, Drop-In Visits, Dog Walking

About: I've grown up around dogs my whole life and have always had a love for them. They have taught me love and responsibility. I also have a horse of my... (more)

18. Victoria

I go above and beyond, every time.

Westfield, MA, 01085

House Sitting, Drop-In Visits, Dog Walking

About: For over 8 years, I have cared for all ages, sizes, breeds, and temperaments of dogs. Keeping your pet happy, healthy, comfortable, exercised, fed,... (more)

19. Erika

social worker and dog lover

Westfield, MA, 01085

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

About: I particularly do not have any history taking care of dogs, but I have grown up with puppies and older dogs as a child through my adulthood. I have... (more)

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

Learn About Premier

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 Chester 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 Chester, 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 Chester pet sitters and avoid the kennel.