Pet Sitting & Drop In Visits in Windsor, 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. Rachael

Full time student part time dog nut

Cheshire, MA, 01225

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

6 repeat clients

About: My life has been dedicated to my dogs and dog sports since I was in elementary school. I've also done pet sitting, dog training, and dog walking fo... (more)

2. Brooke

DOGS=FAMILY

Pittsfield, MA, 01201

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

About: I've had my older dog, Bianca since she was a pup. She's almost 10 now. We just adopted Suki in February of 2016. They're both good dogs, house tra... (more)

3. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

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

4. Charlie-Marie

Ambitious and active dog sitter

Pittsfield, MA, 01201

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

"In the 7 years I have known Charlie, she always had a strong passion for animals, especially dogs. She can't pass by one at the store or out in public wit... (more)"

5. Collette

College Kid Wants to Love Your Dog

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: As a kid, I couldn't wait to visit my grandparents house so that I could play with and help take care of their dogs, Sandy and Kibbles. Since we di... (more)

6. 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)"

7. 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)"

8. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

House Sitting, Drop-In Visits, Dog Walking

"I have found Samantha to be a very knowledgable and careing dog lover that is very conscious of my dogs needs and desires . Samantha has taken care of my... (more)"

9. Kayla

Attentive dog lover will travel

Northampton, MA, 01060

Drop-In Visits, Dog Walking

"Kayla and dogs go together like peas and carrots! She is the epitome of responsibility, and I know when I leave my dog with in her care he'll have a great ti... (more)"

10. Rachael

Full time student part time dog nut

Cheshire, MA, 01225

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

6 repeat clients

"We are happy to report that Rachael took exceptionally good care of our little Caesar! He's on a few supplements and meds, so that gave her a bit more to sch... (more)"

11. Charlie-Marie

Ambitious and active dog sitter

Pittsfield, MA, 01201

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

"In the 7 years I have known Charlie, she always had a strong passion for animals, especially dogs. She can't pass by one at the store or out in public wit... (more)"

12. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

"Ava-Lena is one of the few people in the world who managed to befriend our nervous little rescue dog--and many have tried! We have a two year old daughter an... (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. 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)"

15. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

House Sitting, Drop-In Visits, Dog Walking

"I have found Samantha to be a very knowledgable and careing dog lover that is very conscious of my dogs needs and desires . Samantha has taken care of my... (more)"

16. Collette

College Kid Wants to Love Your Dog

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Collette did a fantastic job with my two pups. I was gone for 10 days, and when I returned home, neither dog was stressed! She cared for my home as if it was... (more)"

17. Mallory

Experienced Pet Sitter at Your Service!

Amherst, MA, 01003

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

5 repeat clients

"Malachi seemed to have a blast with Mallory! We do have a regular dog sitter it we are thrilled to have Mallory as a backup sitter when needed. We felt fully... (more)"

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Learn About Premier

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 Windsor 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 Windsor, 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.