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. Haley

Leave your dog in caring hands!

Southwick, MA, 01077

House Sitting, Drop-In Visits, Dog Walking

About: With having a puppy of my own I know what comes with it and I love everything about having a dog. Not only do I have expierence, but I treat every ... (more)

2. 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)"

3. Laura

Your pet and home are in good hands

South Hadley, MA, 01075

House Sitting, Drop-In Visits, Dog Walking

"Hiring Laura to be your dog sitter is the best decision you can make. She helped me for several years with my sweet Teddy, a 90-lb Chesapeake bay retriever. ... (more)"

Available this weekend
4. Olivia

Responsible and Trustworthy.

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

"Olivia took care of our Wheaten Terrier, Murphy for a week in April of 2017. It was our first time leaving him. Olivia was wonderful and took amazing care of... (more)"

5. Kristin

Home full time, 4 acres yard space

Goshen, MA, 01032

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

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)

6. 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)"

7. Jennifer

love to see dogs happy!

Enfield, CT, 06082

House Sitting, Drop-In Visits, Dog Walking

About: ****UPDATED: my calendar will change once I start working. I will be available for 1 dog walking and 1 drop in visit after 3:30pm on weekdays. I wi... (more)

8. 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)

9. 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)

10. 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)"

11. 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)

12. 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)

13. 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)"

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. Meagan

Difficult Dog? You can trust me!

Greenfield, MA, 01301

House Sitting, Drop-In Visits, Dog Walking

"Meagan has taken care of our 5 dogs and 2 cats on two separate occasions and I can;t think of anyone better qualified of more trustworthy. Meagan has a a wo... (more)"

16. 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)"

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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.