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. 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

"Rachael was very accommodating and willing to take on my Sadie for a few in the middle of the day and evening, fitting my dog into her schedule with very lit... (more)"

Available this weekend
2. Ryan

The Doggie Dood - Pet Services!

Florence, MA, 01062

Dog Boarding, Doggy Day Care

6 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)"

3. Brittany

Loving, responsible & attentive!

Lee, MA, 01260

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

1 repeat client

"Brittany was super sweet and very accomadating! My puppy was happy and well cared for ? (more)"

4. 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)"

5. Brooke

DOGS=FAMILY

Pittsfield, MA, 01201

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

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)

6. 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

"I feel completely confident leaving our dog, Jansen, in Rachel's care. She is trustworthy, thoughtful and obviously knows dogs. She responded within minutes ... (more)"

7. Charlie-Marie

Ambitious and active dog sitter

Pittsfield, MA, 01201

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

"My dogs love Charlie-Marie. She has been dogsitting them for 2 years now. I feel bad leaving them during the day while I am at work or when I go on vacation... (more)"

8. Mallory

Experienced Pet Sitter at Your Service!

Amherst, MA, 01003

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

5 repeat clients

About: Hi there my name is Mallory and I’d LOVE to care for your dog! I have a lot of professional pet care experience and worked as a professional pet ... (more)

9. 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)"

10. Collette

College Kid Wants to Love Your Dog

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

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)

11. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

"Ava-Lena was a wonderful pet sitter to Chuck Norris, our big, loving Saint Bernard. As a pet sitter, Ava was patient, loving, and especially caring to Chuck ... (more)"

12. Kayla

Attentive dog lover will travel

Northampton, MA, 01060

Drop-In Visits, Dog Walking

"Kayla and dogs go together like peas and carrots! She is the epitome of responsibility, and I know when I leave my dog with in her care he'll have a great ti... (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)"

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.