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. Bryan

Dog lover with big farm

Averill Park, NY, 12018

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

2 repeat clients

"Bryan did an awesome job taking care of my puppy, Obi. He was very accommodating with my arrival time in the morning and Obi was always ready to go when I go... (more)"

2. Lydia

I'll go on adventures with your dog

Northampton, MA, 01060

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

3 repeat clients

"Lydia was excellent! I felt comfortable from the initial meeting and then throughout the day, she sent several updates and images of my puppy. Stitch had a... (more)"

3. Kelsey

Home Full Time Pet Sitter

Pittsfield, MA, 01201

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

4 repeat clients

"Kelsey was great. We were staying nearby at Stockbridge and Kripalu and needed our big English Mastiff looked after for the evening. He had a perfect stay ... (more)"

4. 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)"

5. Kristin

Home full time, 4 acres yard space

Goshen, MA, 01032

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

1 repeat client

"Our puppy had so much fun with Kristin and her family, including her dog. Playing all day and spending lots of time outside was great for our dog. Kristin wa... (more)"

6. Melani

Vet Student for Your Furry Friend

Williamstown, MA, 01267

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

1 repeat client

"Melani was just great and would give her an enthusiastic recommendation. Our plan to meet up for Ollie's day of dogsitting went off without a hitch. He clear... (more)"

7. 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)"

8. Melissa

Melissa lives at end of a dirt rd.

Russell, MA, 01071

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

"Great dog sitter! Melissa cared for our dog in her home for nearly two weeks and we were very pleased with the attention and care that she provided. She has ... (more)"

9. Debby

Loving attention in our home

Wilmington, VT, 05363

Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Was worried about leaving our recently rescued dog while we skied since he has some separation issues and found Debbie on Rover and thought some hiking would... (more)"

10. Danielle

10 years of excellent dog boarding!

Pittsfield, MA, 01201

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

About: My name is Danielle and I have been watching dogs forever. I am currently a manager at a local dog daycare and the citys muncipal animal shelter a... (more)

11. Silas

Fenced yard, home during the day

Florence, MA, 01062

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

"Silas is so great with my high energy dog! My dog gets so excited when we tell him Silas is coming. He is also very patient and flexible with my schedule... (more)"

12. Amanda

Fun, Trustworthy,Animal Lover,

Westfield, MA, 01085

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

1 repeat client

"Anyone who knows Amanda knows she is a die hard animal lover, from cats and dogs to fish, rabbits, and horses. She's the type of person that can read animal... (more)"

13. 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)

14. Jane

Walk or Run, it will be done!

Westfield, MA, 01086

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

About: On a brief background knowledge, I study early childhood education in college. I am twenty years old and have my own car. I have had a soft spot i... (more)

15. Chelsea

Multiple daily walks & fenced yard!

Amherst , MA, 01002

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

"Chelsea Smith is so responsible, gentle and loving with all animals. She has taken care of my pets for many years and all I can say is that she is a natural!... (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.