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. Amanda

Fun, Trustworthy,Animal Lover,

Westfield, MA, 01085

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

1 repeat client

"Amanda is wonderful! She connected with our dogs immediately, even one who is a little stand offish. She is trustworthy and we will continue to employ her wh... (more)"

2. Charlie-Marie

Ambitious and active dog sitter

Pittsfield, MA, 01201

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

"In the 7 years I have known Charlie, she always had a strong passion for animals, especially dogs. She can't pass by one at the store or out in public wit... (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. Haley

I absolutely love dogs

Westfield , MA, 01085

House Sitting, Drop-In Visits, Dog Walking

About: I will walk the dogs when they need it and let them out as much as I can if I end up having something to do I make sure I fit the dogs in my schedu... (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. Kate

The best "chuck it arm"in town!

Northampton , MA, 01060

House Sitting, Drop-In Visits, Dog Walking

About: Hello! I'm new to the Rover world of pets and owners, but have plenty to offer. I actively walk and play with a few different dogs in the area but ... (more)

7. 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)

8. Stefan

You pup can count on me.

Northampton, MA, 01060

House Sitting, Drop-In Visits, Dog Walking

"Stefan was employed by me at my dog grooming salon in Newburyport. Not only was Stefan an excellent groomer, he was dependable, responsible, hard working and... (more)"

9. 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)

10. 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)

11. 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)"

12. Kayla

Attentive dog lover will travel

Northampton, MA, 01060

Drop-In Visits, Dog Walking

"Kayla is a dog whisperer! She can charm the orneriest of dogs. She and her own dog companion are absolute soul mates. I have never seen a happier pup. Kayla ... (more)"

13. Carley

Love to run!

Simsbury, CT, 06070

House Sitting, Drop-In Visits, Dog Walking

"Carley is an amazing dog watcher. She has watched my pup many times as well as spending a lot of time romping around the mountains with her. My pup goes craz... (more)"

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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.