Dog Boarding in Winchester

Find a loving dog sitter to watch your dog overnight at your sitter's home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
1. Fatima

Doggies Home & Board

Somerville, MA, 02145

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

2 repeat clients

"Easy to schedule and flexible (my wife and I were later than expected during both drop-off and pick-up). And best of all, Bacon seemed super happy. Would use... (more)"

2. Lissette

Pleasant Pup Inn

Malden, MA, 02148

Dog Boarding, Doggy Day Care

46 repeat clients

"Lisette was a great help taking care of our Carlos during our vacation of 9 days. She was flexible when our flight was delayed and schedule changed, and whe... (more)"

3. Susan

We love dogs like a family member

Burlington, MA, 01803

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

3 repeat clients

"Susan and her family were great to work with! They took amazing care of our lab and treated him like he was part of the family! We will definitely be calling... (more)"

4. Terri

Your Dog's Home away from Home!

Woburn, MA, 01801

Dog Boarding

3 repeat clients

"Loved getting picture updates of our tutti girl! It seems that our pup had a great stay with Terri. She took her for walks and had nothing but good things to... (more)"

5. Melissa

Sleep with a Lady in Arlington!

Arlington, MA, 02474

Dog Boarding

31 repeat clients

"I thought I had posted a review earlier, but must have not done it, so sorry for the delay... Anyway, our beagle had a great overnight experience with Meliss... (more)"

6. Walter

A Dog's Place is in the Home

North Cambridge, Cambridge, MA, 02140

Dog Boarding, Doggy Day Care

45 repeat clients

"Walter did a great job taking care of our dog, Wally. It was so nice to get updates on Wally's stay including pictures of Wally hanging out with the other do... (more)"

7. Sarah

Puppy Retreat on a Quite Street!

Somerville, MA, 02144

Dog Boarding

37 repeat clients

"Sarah and Jon were great with our two pups! They were very accommodating and made our dogs feel at home right away. We will most certainly be using them agai... (more)"

8. Julie

Cuddles, playtime, fun and naps

Woburn, MA, 01801

Dog Boarding, Doggy Day Care

13 repeat clients

"My two Westies had a ball with Julie and her family. They were exhausted when they came home (a tired dog is a happy dog!) They got along great with Julie's... (more)"

9. Candice

Love to teach old dogs new tricks

Somerville, MA, 02144

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

11 repeat clients

"Candice and her two pups were able to accommodate Jake last minute. Candice was super responsive and also sent pictures/updates. Jake seemed to have a great ... (more)"

10. Julie

Dog-loving family

Medford, MA, 02155

Dog Boarding

2 repeat clients

"Great hosts! Shoshi had the time of her life, and we were constantly informed about her situation and received great pics and videos!!! We'll have Shoshi, ou... (more)"

11. Stephanie

Big yard,big heart,playful doggie!

Stoneham, MA, 02180

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

4 repeat clients

"Stephanie was a really good sitter for my pup Bruno. I used Stephanie's boarding services for an early morning to late night schedule. She was very flexible ... (more)"

12. Steve

PAWSitively Pumped 2 Pamper UR Dog!

Somerville, MA, 02145

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

3 repeat clients

"Steve watched our dog Blue for a weekend and did a great job. He was very professional, responded very timely, and his place was well kept. He sent pictures ... (more)"

13. Ryan

Get Your Dog Their Own Room!

Medford, MA, 02155

Dog Boarding, Dog Walking

1 repeat client

"Ryan was a great dog sitter for our 4 year old terrier. From the moment we met him we felt comfortable with him and through the numerous pictures he sent us ... (more)"

14. Rachel

high energy, and active

Neighborhood 9, Cambridge, MA, 02138

Dog Boarding, Dog Walking

9 repeat clients

"Leaving our Zuma with Rachel was a worry-free experience. She kept us up to date with pictures and she was flexible on pick up and drop off times. Zuma got t... (more)"

15. Emily

Auntie Em's Home Away from Home

Arlington, MA, 02474

Dog Boarding

31 repeat clients

"Emily and Rob watched my pup, Denali, for 2 weeks - the longest I've ever left her with someone other than friends or family. While she has a bit of stranger... (more)"

16. Emily

A fan of fetch, hikes, and snuggles


Dog Boarding

5 repeat clients

"Emily was absolutely great! She was attentive, accommodating, and I was very confident that my two dogs were being well cared for while I was away for the w... (more)"

17. Christine & Monica

A Loving Dog Babysitter!

Belmont, MA, 02478

Dog Boarding, Doggy Day Care

14 repeat clients

"This was our first time leaving Addie with Christine and family, but it most certainly won't be the last!! From the initial Meet & Greet all the way through ... (more)"

18. Christine

dog-loving couple on quiet street

Arlington, MA, 02474

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"As we've come to expect, Chrissy was a fantastic keeper for Echo. She sent us frequent puppy picture updates of Echo lounging around with her dog, let Echo s... (more)"

19. Callie

All Dogs Welcome!

Somerville, MA, 02166

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

"Empress LOVED staying with Callie!! She took care of her like she was her own dog. (more)"

20. Kristin

Dog friendly home/yard, dog cuddler

Woburn, MA, 01801

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

"Kristin was by far the best person I have ever left my dog with. Not only did she help me with a last minute overnight stay, she went above and beyond. She p... (more)"

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Learn About Premier

With over 140,000 pet sitters and dog walkers on, we're your one-stop shop for finding and booking trustworthy pet care in Winchester, MA.

Rover offers any pet care you and your pet sitter work out, including:

Dog boarding: You can find a sitter for dog boarding in Winchester easily with Rover. No matter what your pet boarding needs are, you'll find your dog's perfect match right here. Discover, book, and pay for personalized in-home pet boarding all on Rover's easy-to-use site or app. Skip the kennel and book a loving overnight dog boarding sitter on Rover. Your dog will get the individual care and attention they deserve, and you can enjoy benefits like premium insurance, 24/7 support, a secure payment platform, and cute daily photo updates.

Dog walking: Dog walking in Winchester, MA is a breeze to book with Rover. The dog walkers you'll find on Rover offer loving, personalized care and can take your dog everywhere from a hike through the park to a simple stroll around the block. Whatever your dog's speed, there's a dog walker near you on Rover who matches them perfectly. Download the free Rover dog walking app to get started - it's that easy.

Dog Day Care: If you're seeking doggy day care in Winchester, Rover has you covered. You'll find sitters who offer pet day care every day of the week, whenever you need it. When you book with Rover, your dog will get individual attention and care all day long with as many potty breaks as they need. Best of all, the sitters you'll discover and book with on Rover off dog day care near you, right in your neighborhood.

Pet Sitting: Book your next pet sitter in Winchester, MA on Rover. With Rover's pet sitting website and free app, it's easy to discover, book, and pay for your pet's perfect match all on one secure, easy-to-use platform. It doesn't matter how often you need a pet sitter - for a day or a month - you'll find someone who can't wait to drop by and watch your dogs or cats on Rover. You can even check out pet sitter reviews from pet owners just like you to make the right choice for you and your pets.


House Sitting: House sitting in Winchester is a breeze to find and book with Rover. Discover 5-star house sitters right in your neighborhood who can't wait to watch your dog, cat, or virtually any other pet. You'll get the peace of mind of knowing your beloved pets are being cared for in the environment they like best - your home. Plus, booking with Rover's house sitting website gives you tons of added benefits, like premium pet insurance with every booking.