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)"

Confirmed Thanksgiving 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. Sara

Dependable and Active!

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)"

4. 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)"

5. Jenna

Hiking+Walks+Boarding+Day Care

Pittsfield, MA, 01201

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

"Jenna is a dear friend of mine, we have worked together In the dog daycare industry for just over a year now and I am astonished by her care and dedication ... (more)"

6. 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)"

Confirmed Thanksgiving Availability
7. 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)"

8. Taylor

Dog lover with big heart!

Hinsdale, MA, 01235

Drop-In Visits, Dog Walking

"Taylor is a fun and hardworking ray of sunshine. Who better to help you with your family pet than someone who would do anything to make her puppers smile ? R... (more)"

9. 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)"

10. 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)

Confirmed Thanksgiving Availability
11. Hillary

Loving & dependable pet care

North Adams, MA, 01247

House Sitting, Drop-In Visits, Dog Walking

About: Hello there! I'm a huge animal lover with a love for caring for dogs of all kinds. I'm a young professional and I currently work as a youth case ma... (more)

12. Jennifer

Dog trainer w/customizable options

Woodford, VT, 05201

House Sitting, Drop-In Visits, Dog Walking

About: I've worked in several kennels over the past 7 years and worked behind the scenes at a veterinary hospital. For the past 3 1/2 years I worked as a ... (more)

13. 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)"

14. 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)

Confirmed Thanksgiving Availability
15. 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)"

Confirmed Thanksgiving Availability
16. Brooke

Brooke's Dog Sitting

East Greenbush, NY, 12061

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

16 repeat clients

About: ****Send your pup on vacation while you travel :)*** I offer dog sitting in your home as well as mine and I have discounted doggie walks **** Hell... (more)

17. 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)"

Confirmed Thanksgiving Availability
18. 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)"

19. Alexander

Jack of all trades dog friend

North Adams, MA, 01247

House Sitting, Drop-In Visits, Dog Walking

"We've known Alex for several years now and can speak to his personality and ability well. He is someone who puts great care into the details and consistency ... (more)"

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.