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

5 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. Emily

Intuitive Care for High Energy Dogs

Conway, MA, 01341

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

3 repeat clients

"Emily used to take care of our dog, Ellie, when we were away. She is the best dogsitter we've ever had. Each time Emily took care of her, Ellie would come b... (more)"

3. 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)"

4. 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)"

5. Emmett

Vegan w/ love for all things fluffy

Troy, NY, 12182

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

About: I am a young, professional currently working in the non profit world. I have an eleven year vegan with a extreme love for animals! Though I have... (more)

6. 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)"

7. Rachael

Full time student part time dog nut

Cheshire, MA, 01225

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

5 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)"

8. Emily

Intuitive Care for High Energy Dogs

Conway, MA, 01341

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

3 repeat clients

"Emily is AWESOME! And Sampson loves her! She took Sampson on multiple hikes & swims and he was so happy when we got home. (more)"

9. 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)"

10. 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)"

11. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

"Ava-Lena was a wonderful pet sitter to Chuck Norris, our big, loving Saint Bernard. As a pet sitter, Ava was patient, loving, and especially caring to Chuck ... (more)"

12. 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)"

13. 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)"

14. Emmett

Vegan w/ love for all things fluffy

Troy, NY, 12182

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

About: I am a young, professional currently working in the non profit world. I have an eleven year vegan with a extreme love for animals! Though I have... (more)

15. Mallory

Experienced Pet Sitter at Your Service!

Amherst, MA, 01003

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

5 repeat clients

"Mallory watched my German Shepherd Axle this weekend and everything went great! Last minute we needed her for Friday, which hadn't been planned, and she was ... (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.