Pet Sitting & Drop In Visits in Cheshire, 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. Sara

I'll hike with your dog!

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

"Sara is an amazing dog sitter! She watched and help care for my special needs dog, Lexi. Lexi had severe stomach disease and had to stick to a strict diet & ... (more)"

2. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

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

3. Brooke

DOGS=FAMILY

Pittsfield, MA, 01201

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

About: I've had my older dog, Bianca since she was a pup. She's almost 10 now. We just adopted Suki in February of 2016. They're both good dogs, house tra... (more)

4. Katie

Friendly & dependable pet care!

North Adams, MA, 01247

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

1 repeat client

"Katie is my sister, and I have grown up watching her train and take care of plenty of pups, including my own puppy (who may love her more than he loves me!).... (more)"

5. Charlie-Marie

Ambitious and active dog sitter

Pittsfield, MA, 01201

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

"My dogs love Charlie-Marie. She has been dogsitting them for 2 years now. I feel bad leaving them during the day while I am at work or when I go on vacation... (more)"

6. Kathleen

Experienced dog hiker & sitter :)

Townshend, VT, 05353

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

1 repeat client

About: HOUSE SITTING: House sitting is available in VT, NH, MA, and NY. I offer 24hrs a day with your dogs in the comfort of your own home. I will not le... (more)

7. 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)"

8. Collette

College Kid Wants to Love Your Dog

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: As a kid, I couldn't wait to visit my grandparents house so that I could play with and help take care of their dogs, Sandy and Kibbles. Since we di... (more)

9. Emma

A dog depraved college student!

Williamstown, MA, 01267

House Sitting, Drop-In Visits, Dog Walking

"Emma is a very companionate and fun loving girl. She has a deep love for dogs and is a very great owner of her own dog. She constantly makes sure her dog has... (more)"

10. Amber

Veterinary Trained Dog Lover!

Delaware Avenue, Albany, NY, 12209

House Sitting, Drop-In Visits, Dog Walking

About: I grew up with lots of animals. Before and during college, I worked as a veterinary assistant. After college, I volunteered at the humane society. ... (more)

11. Meredith

Petting, play, or pooping? Got it!

Pittsfield, MA, 01201

Drop-In Visits, Dog Walking

"I have known Meredith for several years as she finished college and began working in the Greenville area. She is pleasant and dependable. So when I needed ... (more)"

12. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

House Sitting, Drop-In Visits, Dog Walking

"We have known Sam for many years and she has taken care of our beagle Emmy for the past two years She's is extremely reliable, took the time to get to kno... (more)"

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Learn About Premier

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Cheshire pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Cheshire, MA who meets your — and your pet's — needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet — including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.