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

4 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. 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)"

3. Brooke

DOGS=FAMILY

Pittsfield, MA, 01201

Dog Boarding, Drop-In Visits, Dog Walking

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

4. Taylor

The animals always come first.

Granville , MA, 01034

House Sitting, Drop-In Visits, Dog Walking

"Taylor is a very smart and caring woman who loves caring for all types of pets. She has a sweet disposition and has a lot of experience that allows her to ca... (more)"

5. Luke

3/5 barn builder, 2/5 dog walker

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

About: Hey! I'm Luke! I've cared for dogs all my life. My dog now, Chai Chai, is a sassy princess but we all still love her. Honestly, I can't have enough... (more)

6. Meredith

Petting, play, or pooping? Got it!

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

"We love Meredith! And so do our puppies. She was so thoughtful with both our pets and our home while we were away. She is incredibly kind and reliable, an... (more)"

7. 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)"

8. Rachael

Full time student part time dog nut

Cheshire, MA, 01225

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

4 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)"

9. Taylor

The animals always come first.

Granville , MA, 01034

House Sitting, Drop-In Visits, Dog Walking

"Taylor is dependable and quick to respond at any text or call. I feel fortunate to have found her and you can feel confident in hiring her. She came to my ho... (more)"

10. 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)"

11. Meredith

Petting, play, or pooping? Got it!

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

"Meredith was terrific. Making arrangements was easy and Meredith was great at getting back to us. She sat at our house for 2 weeks, and kept us informed dur... (more)"

12. Mallory

Experienced Pet Sitter at Your Service!

Amherst, MA, 01003

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Like most pet owners, we were very nervous about leaving our girl, Karma, with a stranger. When our usual vacation options were limited, we considered kenne... (more)"

13. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

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)"

14. Luke

3/5 barn builder, 2/5 dog walker

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

About: Hey! I'm Luke! I've cared for dogs all my life. My dog now, Chai Chai, is a sassy princess but we all still love her. Honestly, I can't have enough... (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.