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. Jennifer

I’m Happy keeping your dog happy

Pittsfield, MA, 01201

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

"Jennifer is very connected with my pup and even recommended some training tips. I feel very comfortable knowing that my dog is taken care of while I was am b... (more)"

Confirmed availability
Christmas and New Year
2. 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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3. Beth

I’m loving and playful!!

Dalton, MA, 01226

Dog Boarding, Drop-In Visits, Dog Walking

"Beth is an amazing pet owner and dog sitter. She owns a beautiful Catahoula with her boyfriend and takes the utmost best care of her. She’s always taking her... (more)"

Confirmed availability
Christmas and New Year
4. Bethany

Friendly experience pet lover

Cheshire, MA, 01220

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

"Bethany has watched my dog several times. She always gives Luna the full attention that she needs which is tough because Luna is a high energy husky. Bethany... (more)"

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5. Schuyler

I’ll play with them nonstop

North Adams, MA, 01247

Dog Boarding, Drop-In Visits, Dog Walking

"Schuyler is an incredibly kind and lovable individual, and all the dogs he meets think so as well! He is able to give lots of energy and care to all the dogs... (more)"

Confirmed availability
Christmas and New Year
6. Kelsey

Experienced Pet Care Provider

Pittsfield, MA, 01201

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

"Kelsey is terrific! She loves dogs and my dog loved her. She saved me at the last minute and even came over earlier in the day so we could meet her. We hope ... (more)"

7. 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)"

Confirmed availability
Christmas and New Year
8. Nicole

Animal lover looking for part time

Lanesboro, MA, 01237

House Sitting, Drop-In Visits, Dog Walking

"I have known Nicole her whole life. She adores pets of any kind! She is loving and caring and gentle and has a way with pets I have never seen. Nicole is as ... (more)"

9. 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)"

10. Emma

Big heart and a lot of free time!

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

About: I am a recent college graduated who just moved back home. While searching for some ways to generate extra income, a friend who uses Rover recommend... (more)

11. Magdelin

Will care for your dog as my own ?

Dalton, MA, 01226

Drop-In Visits, Dog Walking

"I NO MAGDELIN WOULD MAKE A WONDERFUL DOG SITTER SHE IS VERY VERY RESPONSIBLE VERY LOVING PERSON AND LOVES DOGS THEY ARE TRULY A PART OF THE FAMILY SHE KIND G... (more)"

Confirmed availability
Christmas and New Year
12. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

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

"Samantha is reliable and responsible. Forrest loves her and I never worry! Thank you Samantha (more)"

13. 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)"

Confirmed availability
Christmas and New Year
14. 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)"

15. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

"Highly recommend! Ava-Lena was so accommodating to our schedule, very responsive and so nice. Absolutely will be using again! (more)"

Confirmed availability
Christmas and New Year
16. Sarah

Doggy Lover thats home full time

Pittsfield, MA, 01201

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

"Sarah P has had several pets throughout her life and has always shown the most loving care and kindness necessary for their care. She understands their need... (more)"

17. 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)"

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18. Jessica

REALLY RELIABLE PET CARE!!

Lenox, MA, 01240

Drop-In Visits, Dog Walking

"Jessica was great and my Yophi just loved her. She would send pictures to us everyday whenever she was taking care of my baby and kept us informed of all her... (more)"

19. 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)"

Confirmed availability
Christmas and New Year
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.