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. 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)"

Confirmed Holiday Availability
2. Kelsey

Experienced Pet Care Provider

Pittsfield, MA, 01201

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

5 repeat clients

"Kelsey was so sweet to our pets and she was very responsive. Would definitely hire again! (more)"

3. Kristin

Home full time, 4 acres yard space

Goshen, MA, 01032

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

2 repeat clients

About: Have owned dogs for over 20 years, pet sit for friends, family, and neighbors. I am over cautious and protective when it comes to animals, I'm also... (more)

4. 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)"

Confirmed Holiday Availability
5. Marge

Dogs are priority

West Springfield, MA, 01089

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

About: I've had dogs all my life and I have 3 Boston Terriers. I treat my dogs like children and I make sure they are happy and well cared for. I have alw... (more)

6. Simone

Work from home, love to run & hike

Hadley, MA, 01035

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I can highly recommend Simone as a responsible, patient, and conscientious animal care-giver. Be it cats or dogs, she can be counted on to follow a pet-owne... (more)"

7. 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)"

Confirmed Holiday Availability
8. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

1 repeat client

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

9. 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)"

10. 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)

Confirmed Holiday Availability
11. Brittany

Always here for you & your kiddo!

Florence, MA, 01060

Dog Boarding, Drop-In Visits, Dog Walking

"I have had Brittany babysit my 12 year old cocker spaniel / poodle mix on numerous occasions. He is somewhat fragile and can be quite sensitive to being touc... (more)"

12. 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)"

13. Lisa

Avid walker and pet- lover

Northampton, MA, 01060

House Sitting, Drop-In Visits, Dog Walking

"I have known Lisa for 12 years, and through different hair styles and music preference, one thing has stayed constant: her passion for animals. Her face ligh... (more)"

14. Madeleine

Love dogs and they love me

Northampton, MA, 01063

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)

Confirmed Holiday Availability
15. Kayla

Animal loving teacher on break!

northampton, MA, 01062

House Sitting, Drop-In Visits, Dog Walking

"Kayla shows an unwavering love for animals and its it evident when ever she is around them. Kayla is also responsible and will put your pet first when tasked... (more)"

16. Romana

Responsible and loveable!

Pittsfield , MA, 01201

Dog Boarding, House Sitting, Drop-In Visits

"Romana is a wonderful person with a real love of animals and knowledge of how to care for them. She is completely committed to caring for your pets. I highl... (more)"

17. Ashley

Dog obsession is an understatement

Southampton , MA, 01073

House Sitting, Drop-In Visits, Dog Walking

"Ashley is the sweetest and she is the biggest animal lover I have ever met! Every time she sees a dog passing by on the street she always has to point it out... (more)"

18. Caitlin

I'll treat you dog as my own!

Westfield, MA, 01085

Dog Boarding, Drop-In Visits, Dog Walking

About: I currently own a cocker spaniel (Cocoa) and a guinea pig (Pippin).I have experience with many breeds and different sized dogs. We go on 1 mile wal... (more)

Confirmed Holiday Availability
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)"

20. 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)


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.