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

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)

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)"

Available this weekend
4. Emily

Intuitive Care for High Energy Dogs

Conway, MA, 01341

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

"Emily is a compassionate person who takes care of the details in her work. She loves animals and treats them with incredible respect and love. Emily loves ... (more)"

5. 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)"

6. Kerry

I get along with all dogs!

Stockbridge, MA, 01262

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Kerry is fantastic with dogs! She is enthusiastic, gentle and patient. She is a responsible individual who keeps commitments and goes above and beyond for ot... (more)"

7. 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)"

8. 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)

9. 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)

10. 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)"

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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.