Dog Boarding in Winsted, CT
Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Top rated Winsted dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“I can’t say enough about how well Sadie was cared for Kristina is certainly a dog-person. She read all the signs that Sadie was giving her to play, train go for a walk and chill. She followed all our directions and cared for Sadie as if she was her own dog. We received a lot of communication in the form of photos and videos. I would highly and without hesitation recommend Kristina to care for your dog too.”

“Couldn’t have ask for a better dog sitter. Loved getting updates and pictures. Daisy was a bit fussy the first day and wouldn’t eat and they made a special treat of chicken and rice to make her happy. Above and beyond any expectations we could have had. Will definitely be using them again. :)”


“This was our dog's first stay with Alan and Luis and we already booked another visit for this summer. They were so nice, responsive, accommodating and communicative - quick responses, sending updates and photos, etc. Laney seemed in great spirits when we picked her up. We are so happy to have found this lovely place!”

“Katie took excellent care of Sadie while we were away on vacation - after meeting her during the meet and greet I felt super comfortable leaving Sadie at her house. Will absolutely use her again for any future vacations, she is quick to respond and very accommodating!”

“Karina was amazing!!! I got stuck in Florida during a snow storm and she had no problem keeping my dog for an extra few days on short notice. She sent daily photos and updates. My fur baby was very well cared for! Karina and Jared will definitely be my go-to dog sitters from now on 😊❤️”

“John and Orie are amazing. They take such good care of our pups when we’re away, whether it’s for a weekend or an extended period of time. One thing we’re super grateful for is their flexibility around timing, and even taking on an additional dog, or adding a night when our plans unexpectedly change! Highly recommend 💚🐕!”

“Contacted James kinda last minute. We met that evening and I dropped my dog off the following night. He must've had fun cause when I picked up up the following evening he was tired from all the playtime. Would definitely use again”


“Kathryn and Jeremy were great, can't recommend them enough. They were extremely communicative both before Bella's stay and during, updating us with pictures etc throughout the day. The couple are very well versed in dog behavior/needs and asked all the right questions to make us feel confident Bella was going to be well cared for and safe. When we picked Bella up she was very comfortable in their home and was resting with Kathryn and Jeremy. If you are looking for trustworthy couple to watch your pup with love and attention, this is it!”

“Haoran was absolutely incredible with our two dogs, Molly and Olive! From start to finish, she went above and beyond with their care. She kept us consistently updated with thoughtful check-ins and photos, which gave us total peace of mind. It was so clear how much she genuinely loves and cares for dogs—Molly and Olive were happy, comfortable, and clearly well loved the entire time. We feel incredibly lucky to have found Haoran and would not hesitate for a second to book with her again. Highest recommendation!”

“Estelle took excellent care of Frannie for the weekend. She was part of the family and I felt reassured and comfortable she was well taken care of and they enjoyed having her there. It is so nice to be able to leave town and not have to worry about your pet. Thank you, Estelle and family!”

“Wonderful couple! They give your pet lots of love and ensure that your pet is happy and well taken care of. They send photos and updates on a regular basis. I would recommend highly to use this couple for dogsitting your loving pet! Amazing! I am definitely having them again!”

“Cruz is a real animal person- she knew how to make my dog very happy and comfortable! Plus she provided pictures while I was away. 10/10.”


“Klaudia was awesome! Our elderly dog had a health crisis while she was caring for him, and she took him to the vet, was very good with communication, and really cared about our guy for 2 days while we made our way home early from vacation. Highest recommendation!!”

About: I’ve been dog sitting for people my whole life. From shitzu’s, to lab mixes. I also have two rescues of my own who I’ve worked very hard with to make comfortable and feel loved after there trauma. I am currently a full time teacher so I’m available mostly weekends. Come summer time, other than a part time job I’ll be available often. I have two high energy dogs who love to play. We do not have a fenced in yard, but it is large with woods all around. We also have a lead set up for dogs who are a flight risk.
“Christle was very good with keeping us updated on how Rosie was doing. This was our first time boarding our puppy and we would go back to Christle again! Rosie even left with a bag full of treats! Thank you so much for watching our Rosie”

About: We are empty nesters (no kids or pets currently in our home), so your pet will get all of our attention. We have been loving dog and cat owners and have taken care of animals our whole lives. We adopted our last dog, Teddy, as a 60 lb one-year-old and raised him to the ripe old age of 17. He was in great health up to the end. We look forward to meeting you and your pet! Tim works from home three days a week, and I work from home full time, so your dog will get lots of attention and frequent walks. We board dogs in our large house in Goshen, CT, with lots of nature around for long walks. And if you have an energetic dog, we'd love to take them with us on nearby hikes.
“Cannot thank them enough. It was my first time using Rover and on a short notice request- no problem. I got pictures of Alfie playing and cuddling throughout his stay which set me at ease. He also came back smelling nicer and was freshly brushed, he was so happy! I 100% recommend Heather and Norman”

“I was so glad to have found Mary Ann on Rover to watch our dog Piper for 2 weeks while we were on vacation. On our initial visit with Mary Ann, I knew this was a great fit for Piper. She is such a sweet, caring, knowledgeable woman that I knew would take wonderful care of my dog. This was the first time using Rover as I was not comfortable leaving her in a kennel again for this long as my dog gets very anxious and sad when we are away and my usual in house dog sitter was with us on vacation. Mary Ann lives just 10 minutes from my house with a lovely fenced in side yard for her to go to the bathroom outside and just run around not being on a leash, which is just like home. Also being able to jump on the furniture and the beds was a plus too, again just like home. And she did not have any issues getting too anxious which is what I was hoping for. It was a perfect fit and a great find. I would not hesitate to book with Mary Ann again.”

“I recently had Gail take care of my dog, Dior, for a week while I was on vacation. The bond Gail and her dog Ginger formed with Dior was heartwarming. It was clear that she genuinely cared for my dog, providing plenty of love and attention. Dior came home happy and well-exercised, which is a testament to the great care they received. Safety was a top priority for me, and I felt completely at ease knowing Gail was watching over my pet. [He/She/They] followed all instructions regarding feeding and I appreciated the regular updates and photos that kept me in the loop. Overall, I couldn't be happier with my experience with Gail. I highly recommend her for anyone looking for a trustworthy and caring dog sitter.”

Over 17 pet parents in Winsted have booked dog boarding
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1. Search
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The median cost per night for dog boarding in Winsted is $50
Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winsted average 11 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of May 2026, the median cost of dog boarding in Winsted is $50 per night, including service fees. Boarding your dog for one week typically costs $350. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Winsted dog boarding rates can be found as low as $26 to as high as $39 per night.
As of May 2026, 374 sitters provided dog boarding in Winsted. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 92% of Winsted dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winsted have an average of 19 years of experience. Dog boarding sitters with repeat customers have an average of 11 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winsted.
Rover makes it easy to find Winsted dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 374 dog boarding sitters in Winsted on Rover, so you’re sure to find the perfect match for your dog! In Winsted, 97% of sitters offer daily exercise, 97% offer medication administration, and 100% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.

