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. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

1 repeat client

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

2. Brooke

DOGS=FAMILY

Pittsfield, MA, 01201

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

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. Katie

Friendly & dependable pet care!

North Adams, MA, 01247

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

1 repeat client

"Katie is my sister, and I have grown up watching her train and take care of plenty of pups, including my own puppy (who may love her more than he loves me!).... (more)"

4. Bethany

Big or small, I've done it all.

Pittsfield, MA, 01201

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

About: I was raised in a family that broke horses and trained dogs. I have worked at multiple doggie daycares, and am not intimidated by any dog ... or nu... (more)

5. Kristin

Home full time, 4 acres yard space

Goshen, MA, 01032

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

About: Have owned dogs for over 20 years, pet sit for friends, family, and neighbors. I am over cautious and protective when it comes to animals, I'm also... (more)

6. Kate

The best "chuck it arm"in town!

Northampton, MA, 01060

House Sitting, Drop-In Visits, Dog Walking

About: Hello! I'm new to the Rover world of pets and owners, but have plenty to offer. I actively walk and play with a few different dogs in the area but ... (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. 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)"

9. 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)

10. 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)"

Available this weekend
11. 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)"

Available this weekend
12. Olivia

Responsible and Trustworthy.

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

"Olivia took care of our Wheaten Terrier, Murphy for a week in April of 2017. It was our first time leaving him. Olivia was wonderful and took amazing care of... (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

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.