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.

Calendar Recently Updated
1. Kelsey

Experienced Pet Care Provider

Pittsfield, MA, 01201

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

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

2. Heather

Home Full-Time Flexible Hours

Pittsfield, MA, 01201

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

"Heather took care of our dog, Cal, during a brief trip out of town. She was friendly, was easy to reach, and sent us the most adorable photos during her vis... (more)"

Calendar Recently Updated
3. Carolyn

IT'S ALL ABOUT THE SNUGGLE

Jacksonville, VT, 05363

House Sitting, Drop-In Visits, Dog Walking

"I have known Carolyn for over 40 years. She is one of the most compassionate, attentive animal lovers I have ever met. She genuinely loves all animals and tr... (more)"

Calendar Recently Updated
4. Sara

Dependable and Active!

Pittsfield, MA, 01201

Dog Boarding, Drop-In Visits, Doggy Day Care

"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)"

5. Alyson

Flexible schedule, love walking

Dalton, MA, 01226

Drop-In Visits, Dog Walking

"I felt Very comfortable with Alyson come to let the dogs out for a bit. I’m so glad we found her and will definitely be booking with her again. (more)"

Calendar Recently Updated
6. Kaylee

Dependable, reliable, & dog loving

North Adams, MA, 01247

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

"Kaylee and Lindsey took great care of Gypsy and Jake, and we really appreciated the updates and photos. Highly recommended. (more)"

7. 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)"

8. Angela

Large Yard for Big Play Times!

Shelburne falls, MA, 01370

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

"Our family has know Angela for years. We travel several times a year for at least a week and always ask her to take care of our animals. We have a dog, two ... (more)"

9. Mary

Dog lover! I live on a 8 acre farm

Hoosick falls, NY, 12090

House Sitting, Drop-In Visits, Dog Walking

About: I can do all, graduate of equine science I enjoy working with animals and have had dogs my intire life. I’ve taken care of lots of kinds of animals... (more)

Calendar Recently Updated
10. Kira

Dog walker, runner, or hiker!

Lenox, MA, 01240

Drop-In Visits, Dog Walking

"Kira is terrific! She is very responsible and Roscoe loves seeing her come to visit. It’s huge peace of mind for me knowing that he will be in such good hand... (more)"

Calendar Recently Updated
11. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

Dog Boarding, 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)"

Calendar Recently Updated
12. Ashley

I'll run and play with your dog!

Bennington, VT, 05201

Drop-In Visits, Dog Walking

"Ashley combines a customer service background with a genuine love for animals. I've personally seen her go to great lengths for animals, hers or others, just... (more)"

Calendar Recently Updated
13. Holly

Know all the best dog walking spots

Williamstown, MA, 01267

House Sitting, Drop-In Visits, Dog Walking

"Holly F. is a reliable and flexible dog walker and sitter. She is comfortable with all dogs and extremely accommodating of all of their needs. I highly recom... (more)"

14. 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)"

15. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

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

16. 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)"

17. Kody

Reliable and flexible dog lover!

North Adams, MA, 01247

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

"Where do I begin. Kody is a special kind of person. A truely unique blend of kindness, care, and selflessness that isnt frequently found these days. I own a ... (more)"

Confirmed availability
This weekend
18. Emily

Willing to love on your dog 24/7

Cummington, MA, 01026

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

About: I love dogs and cats and the unconditional love they give back in return. I want to show your pet that love when you unfortunately can’t be home to... (more)

19. Kelly

Family of dogs love them like mine

Stephentown, NY, 12168

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

About: Worked fostering dogs for over 20 years and my mom was a vet tech we have always loved our animals like family they bring so much joy to our lives.... (more)

20. Brandon

Loving care for your pet

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

About: I have had dogs in my house for the last 15 Year’s. I currently take care of two of my own. I enjoy taking my dogs on hikes on various trails aroun... (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.