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. 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)"

Confirmed New Years Availability
2. Sara

Dependable and Active!

Pittsfield, MA, 01201

House Sitting, Drop-In Visits

"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)"

Confirmed Holiday Availability
3. Kelsey

Experienced Pet Care Provider

Pittsfield, MA, 01201

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

5 repeat clients

"Kelsey was so sweet to our pets and she was very responsive. Would definitely hire again! (more)"

4. Kristin

Home full time, 4 acres yard space

Goshen, MA, 01032

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

2 repeat clients

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)

Confirmed Holiday Availability
5. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

1 repeat client

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

6. Stefan

You pup can count on me.

Northampton, MA, 01060

House Sitting, Drop-In Visits, Dog Walking

"Stefan was employed by me at my dog grooming salon in Newburyport. Not only was Stefan an excellent groomer, he was dependable, responsible, hard working and... (more)"

7. 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)"

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)"

Confirmed New Years Availability
9. Meredith

Petting, play, or pooping? Got it!

Pittsfield, MA, 01201

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)"

10. Heather

Home full-time - Ready to play

Lake Pleasant, MA, 01347

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

About: I love dogs and taking care of them no matter the size. I am available 7 days a week any time of day and will be available to come to your home and... (more)

11. Michael

Friendly guy, to both people & dogs

Florence, MA, 01062

House Sitting, Drop-In Visits, Dog Walking

"Such is Michael's love for pups that that is what I call him - Pup! Pup speaks often and lovingly of the pup of his youth, Kasha, a handsome Samoyed with reg... (more)"

Confirmed Holiday Availability
12. Brooke

Brooke's Dog Sitting

East Greenbush, NY, 12061

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

17 repeat clients

About: ****Send your pup on vacation while you travel :)*** I offer dog sitting in your home as well as mine and I have discounted doggie walks **** Hell... (more)

13. 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)"

14. 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)"

Confirmed Holiday Availability
15. Taylor

The animals always come first.

Granville, MA, 01034

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)"

16. Jennifer

Dog trainer w/customizable options

Woodford, VT, 05201

House Sitting, Drop-In Visits, Dog Walking

About: I've worked in several kennels over the past 7 years and worked behind the scenes at a veterinary hospital. For the past 3 1/2 years I worked as a ... (more)

17. Amber

Veterinary Trained Dog Lover!

Delaware Avenue, Albany, NY, 12209

House Sitting, Drop-In Visits, Dog Walking

About: I grew up with lots of animals. Before and during college, I worked as a veterinary assistant. After college, I volunteered at the humane society. ... (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 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.