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. Jessica

If ur pup needs company- choose me

Holyoke, MA, 01040

House Sitting, Drop-In Visits, Dog Walking

"Jessica did drop in visits at my place for my Yorkie, Oliver! She kept me informed on everything with reports and pictures every visit...was very loving and ... (more)"

2. Briana

Got a big one? Experienced XL breed

Russell, MA, 01071

Drop-In Visits, Dog Walking

"Hello I'm Michael one of Bri's closest friends and I want to assure you why Bri is perfect for the job as a dog handler. She is a dog lover in specific and a... (more)"

3. Lisa

Avid walker and pet- lover

Northampton, MA, 01060

House Sitting, Drop-In Visits, Dog Walking

"Lisa was wonderful. She took great care of our cat while we were on vacation, kept in regular communication, and sent us lots of pictures. We will definite... (more)"

4. Courtney

Energetic Walker!

Westfield, MA, 01085

Drop-In Visits, Dog Walking

"Simply put, Courtney is fantastic with dogs and has a real presence with them. She has a natural knack for putting them at ease and would not be intimidated ... (more)"

5. Lucie-Ann

Affordable and reliable pet lover!

Northampton, MA, 01060

House Sitting, Drop-In Visits, Dog Walking

"Lucie-Ann was great. Very responsive and easy to work with. She took great care of my cats while I was out of town for a week and sent me better pictures of ... (more)"

6. Rosa

Enjoys long walks through the woods

Northampton, MA, 01060

Drop-In Visits, Dog Walking

About: Hi there! My name is Rosa. I am an artist, so I try to balance expenses with many part time jobs. I have a flexible schedule and love being out... (more)

7. Erin

Pet owners make friends furrrever

Southampton, MA, 01073

House Sitting, Drop-In Visits, Dog Walking

"Erin is just wonderful with our dog!! She is attentive, sweet and knowledgeable! She works hard to make our dog feel loved, important and fit. She gives grea... (more)"

8. Amanda

Fun, Trustworthy,Animal Lover,

Westfield, MA, 01085

House Sitting, Drop-In Visits, Dog Walking

"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)"

9. 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)"

10. Dave

Experienced / flexible. Fun 4 dogs

Hatfield, MA, 01088

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

"I’ve never met a dog who didn’t love Dave. Dave is fluent in dog, and seems instantly able to calm even the most agitated pup. He’s also a clear communicator... (more)"

11. Amy

In Love with Animals- Flexible

SOUTHAMPTON, MA, 01073

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

"Amy has been a volunteer for the Westfield Homeless Cat Project for several years. She has fostered kittens and does a fabulous job. I wouldn't hesitate to... (more)"

12. Ava

Home full time - Parks nearby!

Williamsburg, MA, 01096

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

About: My name is Ava and I am a college student home for the summer. I’m hoping to buy a car soon and am looking to save up some money. Once I graduate I... (more)

13. Sara

Dogs think I'm one of them.

Florence, MA, 01062

House Sitting, Drop-In Visits, Dog Walking

"I have known Sara for 35 years. She is an extremely reliable and compassionate caregiver to animals. Recently she met my dog, and Garnet (who is usually shy ... (more)"

14. Madeleine

Love dogs and they love me

Northampton, MA, 01063

House Sitting, Drop-In Visits, Dog Walking

About: I took care of a cat for at least 8 years and have taken care of my friends dogs before. This summer I have been helping my friend pet sit and almo... (more)

15. Ashley

Dog obsession is an understatement

Southampton , MA, 01073

House Sitting, Drop-In Visits, Dog Walking

"Ashley has watched our dog, Lucy and she was the best. She took her on walks, sent us pictures and made sure she was well taken care of. She is an obvious ... (more)"

16. 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)"

17. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

"Very professional and saved me in the last minute! (more)"

18. David

Recently retired and loving dogs

Florence, MA, 01062

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

"I texted David last minute to see if he could take my pup Maddie for a walk. He was quick to respond and was thankfully available. He went over right away an... (more)"

19. Taylor

The animals always come first.

Granville, MA, 01034

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)"

Available this weekend
20. Emily

Willing to love on your dog 24/7

Cummington, MA, 01026

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

About: I love dogs and cats and the unconditional love they give back in return. I want to show your pet that love when you unfortunately can’t be home to... (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 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.