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. 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)"

2. Sara

I'll hike with your dog!

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

"Sara came to our resort unit on Sunday before the sitting day we needed which was Thursday. There was some confusion as to the times she would be available.... (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

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. Kelsey

Home Full Time Pet Sitter

Pittsfield, MA, 01201

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

1 repeat client

About: Hi there! I am at home full time pet care provider. I was lucky enough to be raised around animals and parents that encouraged my passion. I hav... (more)

5. Andrea

Playful walks and plenty of kisses!

Hinsdale, MA, 01235

House Sitting, Drop-In Visits, Dog Walking

About: My name is Andrea. I live with my sister and our big furry cat named Odin, who was a local stray. I have been a pet owner my whole life and love al... (more)

6. Danielle

10 years of excellent dog boarding!

Pittsfield, MA, 01201

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

About: My name is Danielle and I have been watching dogs forever. I am currently a manager at a local dog daycare and the citys muncipal animal shelter a... (more)

7. 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)"

8. 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)"

9. Bethany

Big or small, I've done it all.

Pittsfield, MA, 01201

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

1 repeat client

About: I was raised in a family that broke horses and trained dogs. I have worked at multiple doggie daycares, and am not intimidated by any dog ... or nu... (more)

10. 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)"

11. Danielle

Life's always better with a dog!

Valatie, NY, 12184

House Sitting, Drop-In Visits, Dog Walking

"Danielle took great care of my dog. We would definitely use her again. (more)"

12. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

1 repeat client

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

13. Millie

I will love yours like I love mine!

Pine Hills, Albany, NY, 12203

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

About: My pet style is to treat each of your precious pets like my own, with love, care and respect. You can count that I will be there when I say I will... (more)

14. 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)"

15. 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)

16. 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)

Available this weekend
17. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

House Sitting, Drop-In Visits, Dog Walking

"I have found Samantha to be a very knowledgable and careing dog lover that is very conscious of my dogs needs and desires . Samantha has taken care of my... (more)"

18. Alexander

Jack of all trades dog friend

North Adams, MA, 01247

House Sitting, Drop-In Visits, Dog Walking

"Alex has a great deal of patience that shines through when caring for dogs. His experience growing up in a family of boxer breeders makes him comfortable wit... (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.