Doggy Day Care in Windsor, MA

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

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 was wonderful: easygoing, flexible, accommodating and considerate. She took first-rate care of our dog, Pip, and made our visit to Mass MoCa not only p... (more)"

2. Silas

Fenced yard, home during the day

Florence, MA, 01062

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

"Silas has watched my dog, Odin (a 4 year old Norwegian Elkhound), several times since I've owned him. He would actually come to my house during work hours wh... (more)"

3. 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)

4. Ryan

The Doggie Dood - Pet Services!

Florence, MA, 01062

Dog Boarding, Doggy Day Care

9 repeat clients

"Excellent care. Maya really loved her time with Ryan and especially with his dog, Willow! She was quite happy and tired when I got her home. (more)"

Available this weekend
5. 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)"

6. 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)

7. 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 was fantastic! She tools great care of our two pups. She kept us updated with photos and summaries of her time with them. Will definitely use her again. (more)"

8. 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)

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. 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)

11. 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)"

12. 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)

13. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

1 repeat client

"Ava is a dream with our boys! She made them so happy in our home and consistently kept in touch. Our pups were well cared for and so was our home. We are so ... (more)"

14. 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
15. 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)"

Experience exceptional service and a personalized match

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

Learn About Premier

With Rover, you can find a trustworthy, loving pet sitter to take care of your dog while you're at work or have a day full or errands. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more 40,000 sitters who've listed their services on Rover. That way, you're sure to find a doggy day care who's right for your needs. We're proud that 95% of our sitters have 100% 5-star reviews, and we think your dog will love them too. Search for a sitter who offers doggy day care, schedule a Meet & Greet, and book the stay if it seems like a good fit. No matter how often you need day care, you're sure to find a sitter who will treat your dog like family.