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

Large Fenced Yard - Flexible Hours

Pittsfield, MA, 01201

Dog Boarding, House Sitting, 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)"

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2. Danielle

Huge yard and tons of play time!

New Lebanon, NY, 12125

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

"Danielle is great! She’s extremely friendly, very responsive to messages and was super flexible/accommodating to the drop-in schedule we needed. Absolutely r... (more)"

3. 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)"

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4. 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)"

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5. Joshua

My pup and i love walks!

North adams, MA, 01247

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

"Joshua is by far the most amazing pet sitter ever, even the woofers pick up on it and love his presence so much! He is very responsible and safe when taking ... (more)"

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6. Lindsay

I will give your dogs ALL the love

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

"Lindsay is our go to pet sitter anytime we are away, no matter how long we are going to be gone. I always know that our two cats and three dogs are going to ... (more)"

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This weekend
7. Emily

Willing to love on your dog 24/7

Cummington, MA, 01026

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

"Emily was a pleasure to work with. I highly recommend her :) (more)"

8. Morgan

Animal lover -Large fenced in yard

Pittsfield, MA, 01201

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

"Morgan is a terrific dog sitter. Since she was young she has always cared and watched over the fur babies in our family. She has a way with them like no ot... (more)"

9. 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)"

10. Sara

Dependable and Active!

Pittsfield, MA, 01201

Drop-In Visits, Doggy Day Care, 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)"

11. 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)"

12. 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)"

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13. 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)"

14. Julia

I love dogs more than anything.

Williamstown, MA, 01267

House Sitting, Drop-In Visits, Dog Walking

"Julia is one of the most tender, attentive people I know. I have seen her care for and connect with many dogs and have not only seen how happy she is with pu... (more)"

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15. Tarryn

Vet tech and animal lover

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

"I felt very comfortable leaving my dog with Tarryn. She is very professional. She gave me updates on my pup with pictures while I was away. She left my house... (more)"

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16. Bethany

Big or small, I've done it all.

Pittsfield, MA, 01201

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

About: I grew up training dogs my family bred, grooming, and even breaking horses. I've worked at a doggie daycares. I understand the need for a specific ... (more)

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17. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

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

"Our girl has a home <3 away from home! She is very loved and cared for by Samantha! :) Thank you again for taking her short notice! 5 star & beyond <3 (more)"

18. 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)"

19. 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 managed a local dog daycare and boarding facility and spent 7 years managing the city... (more)

20. 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)

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.