Dog Boarding in Winsted, CT
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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.
“Being that this was Hannah's first experience away from us, and with the separation anxiety she has, Karina showed a lot of patience and compassion in helping Hannah feel at home. I would highly recommend her if you are in need of a sitter.”

“Kristina and Jordan took such amazing care of my pup while I was away. Kristina and Jordan treated her with so much love, and sent many pictures and videos during the stay. I’m definitely an anxious pet parent, but their care actually allowed me to relax knowing that she was in the best hands possible and having a great little vacation of her own. I couldn’t recommend them more. Thank you guys so much!”


“Outstanding! Alan and Luis provided extraordinary care for our Black Lab mix Annie while we were on vacation for a week. They are truly the best! Compassionate, friendly, caring, trustworthy are just a few words to describe Alan and Luis. The house is beautiful with a gated fence and a "kiddy pool". Annie truly enjoyed her stay and playing with the other guests as evidenced by her disposition when I picked her up and the the daily photos. I will always check first with Alan and Luis in the future when I need a sitter for Annie.”

“I'm so happy I found Angela (khanh) and Tommy before traveling halfway around the globe. After our meet and greet I knew I could relax on vacation knowing my pup was in good hands. Angela has that motherly instinct for all dogs big and small, and Tommy is an experienced dog groomer. I got picture and video updates everyday, I felt like my dog was at summer camp and she would never want to come home! I know she got lots of love and exercise and she will be coming back again.”

“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!”


“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!”

“From the first contact, I loved James' response. He first asked about meeting Neo to see if he would be a good match for his family, which gave me peace. He kept in contact by sending us pics and updates during our time away. No regrets! 🙏🏻”

“Maria has watched our senior lab twice - one with home visits and once boarding. Both times we returned home to a happy healthy dog. She is very thoughtful and always has our dog’s best interest in mind. We will continue to use her as a great alternative to the kennnel.”
“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.”

“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!”


“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!!”

“Mary Ann was absolutely wonderful to work with! She watched our elderly blind and diabetic dog for us during a weeklong trip, and the peace of mind we felt knowing that our dog was so well cared for was such a gift. Mary Ann took time to do a meet and greet before our trip so that our dog could get to know her and her property, and so that she could take detailed notes on our dog’s needs. We also received periodic updates while we were away. Mary Ann truly goes above and beyond, and we will gladly request her services again when the need arises! Thank you!!”

“Hoaran was great and her communication was excellent! We appreciated that she took Roman to the dog park to make new friends! She took lots of photos and made my husky feel like he was part of that gang! He can’t wait to hang with Hoaran again!”

“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!”

“I would like to thank Jaylese for her love and care, she is extremely careful and attentive and took great care of our Enzo!! And she accepted our dog on the last minute Very thankful I highly recommend it and he will definitely come back again ♥️”

“Ifan was a great sitter for our big boy Dom. He was very good with communication both before and during the sit. He sent pictures and updates about how Dom was doing and all pertinent information. He was very accommodating with our flexible schedule and wr truly appreciated that. We would definitely utilize his services again and we would recommend him for anyone looking for a top notch sitter.”

“Allison was great with watching our dog! We had a short notice request and she was able to communicate effectively and efficiently what would work with her schedule along with ours. She sent updates and photos regularly. Our dog had tons of fun running around in her fenced in yard! Thanks again Allison. 10/10 recommend.”

“Adrienne took very good care of our baby and treated her as if it was her own. Our dog had a wonderful time staying with her. She sent lots of updates throughout the day which made us feel very comfortable. Thank you!”

Over 18 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
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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.
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We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winsted average 12 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Jun 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 $32 to as high as $109 per night.
As of Jun 2026, 694 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, 91% of Winsted dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winsted have an average of 18 years of experience. Dog boarding sitters with repeat customers have an average of 12 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 694 dog boarding sitters in Winsted on Rover, so you’re sure to find the perfect match for your dog! In Winsted, 99% of sitters offer daily exercise, 97% offer medication administration, and 96% 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.


