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 is a very kind young woman who clearly just loves dogs. Her home is filled with dogs, she's a dedicated dog agility trainer and my dog had a great t... (more)"

2. Melani

Vet Student for Your Furry Friend

williamstown, MA, 01267

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

"Melani was completely reliable and took perfect care of my dog! (more)"

Available this weekend
3. 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)"

4. 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)"

5. Brittany

Loving, responsible & attentive!

Pittsfield, MA, 01201

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)"

6. 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)

7. 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)"

Available this weekend
8. Emily

Intuitive Care for High Energy Dogs

Conway, MA, 01341

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

"Emily came and watched my dog and two cats while I was on a trip and did a wonderful job! She was very flexible, sent me some pictures and updates, and Blue ... (more)"

9. 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)"

10. 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)"

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. 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)

13. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

"I whole-heartedly and unhesitatingly recommend Ava. She has babysat and done many other things for me off and on, including pet-sitting, for at least 8 years... (more)"

14. 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)

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.