Doggy Day Care in Cheshire, MA

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

Confirmed availability
Labor Day
1. Jeanne

Country setting, lots of hiking

pittsfield, MA, 01201

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

"Jeanne is awesome. She took Romeo on great adventures and gave him lots of attentionm. I would give six stars if I could! (more)"

Confirmed availability
Labor Day
2. Patty

Home full time - Play & snuggles!

Rensselaer, NY, 12144

Dog Boarding, Drop-In Visits, Doggy Day Care

"Dervish had a great stay with Patty. Patty took very good care of our elderly Corgi. He returned home calm and rested. We got lots of cute photos from Patty ... (more)"

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3. Ashley

large walking area , play with dogs

Troy, NY, 12180

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

About: I love animals overall but i prefer dogs especially they are so sweet and caring, and they just warm my heart! I've owned dogs for as long as i can... (more)

Confirmed availability
Labor Day
4. Jillian

Home full time-large fenced yard

Watervliet, NY, 12189

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

"Jillian is awesome!! Buffy had a great time and was exhausted when she came home. Already have another sitting booked with Jillian!!!! A+++ (more)"

Confirmed availability
Labor Day
5. Tess

Full time stay at home mom/dog mom!

Albany, NY, 12204

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

"Tess is great and Phoebe loves going to daycare! She comes home happy and exhausted. A+ (more)"

Confirmed availability
Labor Day
6. Debra

Your dog will always be happy!

Troy, NY, 12180

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

"Thanks for taking such good care of Hank! He must have had a great time with Snoopy because he is zonked out on my couch snoring. LOL (more)"

Confirmed availability
Labor Day
7. Bryan

Dog lover with big farm

Averill Park, NY, 12018

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

"Koda had a great time. Im a first time dog mom so i was worried about koda and Bryan sent me pics and updates everyday. Thank you so much. Koda cant wait to ... (more)"

8. Catherine

Doggy Trails is where we like to Go

New Lebanon, NY, 12125

Dog Boarding, Drop-In Visits, Doggy Day Care

"Catherine is great with all animals but most importantly with dogs!!! I have 6 dogs and it's always been a challenge to find a pet sitter that is trustworthy... (more)"

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9. Jason

Short fores hikes / village strolls

Williamstown, MA, 01267

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

"Jason is a great friend to animals. I have seen him personally rescue and rehabilitate a number of critters. He has watched my African Gray, cats and dogs wh... (more)"

Confirmed availability
Labor Day
10. Danielle

Home full time! Huge yard!

New Lebanon, NY, 12125

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

"Danielle has cared for my dogs and cat for the past five years. I trust her immensely and am able to have full confidence that my furbabies will be loved an... (more)"

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11. Kody

Reliable and flexible dog lover!

North Adams, MA, 01247

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

"Where do I begin. Kody is a special kind of person. A truely unique blend of kindness, care, and selflessness that isnt frequently found these days. I own a ... (more)"

12. Paige

I already know I’ll love your dog!

East Chatham, NY, 12060

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

"Paige was great! Very responsive and sent lots of updates. Our dog really liked her and came home tired out. We will definitely be booking with Paige again i... (more)"

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13. Kelly

love spending time with dogs!

Great barrington, MA, 01230

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

About: My history would be that I've grown up with dogs my whole life. There has never not been a dog in my household and if i could spend all of my time ... (more)

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14. Terry

My dog is my best friend

Watervliet, NY, 12189

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

"Terry is great!!! She responds very quickly and is super responsible. She asked me everything to make my dog feel as comfortable as possible. She not just to... (more)"

15. Angela

I live as a full time doggie mom.

Troy, NY, 12182

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

"Thank you for taking such good care of Jemma! We will definitely contact you again! (more)"

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16. Adrianna

Home full-time, large backyard

Troy, NY, 12180

Dog Boarding, Doggy Day Care

"Hank had a great time, thanks for taking care of my doggo! (more)"

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17. Acacia

Small yard big heart care

Troy, NY, 12180

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

"Acacia has been an animal lover since I met her in elementary school. She has helped take care of my pups for years , she is a second mom to all of them :) ... (more)"

18. Mary

Swimming and Hiking!

Troy, NY, 12180

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

"Mary came over to take care of my dogs while i was on vacation. They love her! She brought them to grooming appointments and to the lake to swim and for a lo... (more)"

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19. Carol

Professional Dog Trainer

Hoosick Falls, NY, 12090

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

"BOY CAN I TELL YOU ABOUT CAROL LOVES ANIMALS MORE THAN LIFE IT SELF TAKES THE TIME TO GO THE EXTRA STEPS LISTENS TO THE PETS AND THERE OWNERS NEEDS WILL MAKE... (more)"

20. Lauren

I absolutely love animals!

Troy, NY, 12180

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

About: I adore animals of all shapes and sizes. I have been watching the pets of my friends and family for years now. It’s my favorite hobby by far! The o... (more)


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.