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. Heather

Home Full-Time Flexible Hours

Pittsfield, MA, 01201

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

1 repeat client

"We couldn’t be more pleased! Heather does drop-in visits for us to care for our German Shepherd when we’re away and there’s nothing like being able to leave ... (more)"

Confirmed Memorial day Availability
2. Angela

Large Yard for Big Play Times!

Shelburne falls, MA, 01370

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

3. Kelsey

Experienced Pet Care Provider

Pittsfield, MA, 01201

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

6 repeat clients

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

4. Lauren

Home full time, tons of land!!

Johnsonville, NY, 12094

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

"My experience with Lauren has been great! She's a wonderful pet sitter and my dogs love her. They were well cared for and I don't think they even missed me! (more)"

5. 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)"

Confirmed Memorial day Availability
6. Cassidy

full time animal lover

Nassau, NY, 12110

House Sitting, Drop-In Visits, Dog Walking

About: Growing up i've always been surrounded by animals which really sparked my love for all animals. And since i was 12 i've pet sat for neighbors and f... (more)

7. Mary

Dog lover! I live on a 8 acre farm

Hoosick falls, NY, 12090

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

1 repeat client

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)

8. Nicole

Dog Lover!

North Adams, MA, 01247

Drop-In Visits, Dog Walking

"Nicole is a responsible, smart, & an animal loving young lady; she and her family have had pets her entire life. She comes from a multi-household pet home w... (more)"

9. Nathan

I'll take your dog to the park

Weststockbridge, MA, 01266

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

About: I love animals I'm kind and friendly I am respectful and responsible. I will keep your dog happy and we will become friends. I've had dogs througho... (more)

10. Idaliz

All Dogs Welcome

North Adams, MA, 01247

Drop-In Visits, Dog Walking

About: I have had experience working with a variety of animals including, but not limited to, cats, dogs, chickens, goats, cows, pigs, guinea pigs, lizard... (more)

11. Brooke

Brooke's Dog Sitting

East Greenbush, NY, 12061

Dog Boarding, Drop-In Visits, Dog Walking

22 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)

12. 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)"

13. Kristin

Home full time, 4 acres yard space

Goshen, MA, 01032

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

4 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 Memorial day Availability
14. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

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

"Samantha is a very dependable, friendly, and caring person, who really took great care of our 3 dogs when we went on vacation. Whether it was just for the we... (more)"

15. Jennifer

Dog lover willing to travel!

Rensselaer, NY, 12144

House Sitting, Drop-In Visits, Dog Walking

"Jennifer was wonderful! All of our animals were well taken care of and our house was in perfect condition when we got home from out 10 day vacation to Florid... (more)"

16. 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)"

17. Lauren

Training and care experience!

Greenfield, MA, 01301

House Sitting, Drop-In Visits, Dog Walking

"Lauren was prompt and professional, she is an excellent sitter. (more)"

18. 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)"

19. 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)"

20. Kody

Reliable and flexible dog lover!

North Adams, MA, 01247

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

1 repeat client

"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)"

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.