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

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Top rated Windsor dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Estrella loved going to Sarah's house! She always has a fun time playing with Sarah's dogs and she met a new friend in the regular daycare dog they host. We got lots of adorable pictures and videos and Estrella came home tired and happy!”

“Edith was amazing, as always. She provided frequent updates and photos of Henry throughout our 10-day holiday, which we truly appreciated. We always feel completely at ease knowing Henry is in such good hands with Edith—she takes wonderful care of him and clearly makes sure he’s happy and having a great time. Because of her, we’re able to fully relax and enjoy our trip without a single worry.”

“Ronalisa is very kind. She has a really nice yard for Spunky and Boss to run around. Very responsive. My dogs enjoyed their staycation with her and her fur babies. Spunky and Boss came home tired and happy. Recommend her 10/10.”

“Gilian was a fantastic sitter and gave tons of attention to my dog throughout the whole process. She gave extremely thorough updates and her system provided my dog with lots of socialization which made me feel more comfortable while I was gone. I would not hesitate to leave my dog in her care again.”

“Val watched My dog Bentley over night and he seemed to enjoy himself. He was. He was nice and tired when I picked him up so I'm sure he had a good time with the other dogs as well. I will definitely use Val in the future to watch my pup.”
“Rebecca and Connor took great care of Tula and sent tons of pics and videos! Would def seek them out to board Tula again! The house is very pet friendly and Tula enjoyed the basket of toys :)”
“I've always been worried about having someone watch my dog because I'm always worried he can be a handful, but he did so well with Joan! She was very quick to respond to my request as I had to find a sitter last minute and she took great care of him and was attentive to his needs like his oral medication. Her dogs are very well behaved and were great company for him! He also had a lot of fun with another dog that was over for doggie day-care. Overall a great place for him to be since he loves to have company! She sent a lot of very cute pictures of him with the other dogs and was very flexible with me when I had an emergency and wouldn't be able to pick him up on time. If I ever need someone to dog-sit for me again I will definitely ask Joan!”

“Such a treat to have Duane & Lauren take care of my pup, Rapha while I was away. They are very responsive and attentive to the needs of both owner and doggie. Thank you!”

“Kaycee was very helpful at our meet and greet, we hung out in their yard for a bit and she explained their setup and routine. She sent pictures while Ollie was boarded, which is much appreciated, and accommodated Ollie when he needed company overnight.”

“Absolutely wonderful experience having our two pups stay with Erik and his family. Extremely communicative, kind and accommodating through the process. Would HIGHLY recommend to anyone worried about hosts looking after their loved pets.”

“Alexander and Hannah did a great job with Cannoli! They were flexible and understanding and tried to ensure she was as comfortable as possible during her stay. I appreciated that they allowed her to sleep in the bed with them to ease her anxiety about being in a new place.”

“Lindsey did a fantastic job of taking care of Coco. During my trip, I had travel delays and Lindsey was more than accommodating to help with last minute changes. She gave me frequent updates on Coco and I felt very at ease knowing that my fur baby was in very good hands. Would highly recommend!”

“Jessica and her kiddos were great to my dog! He got along well with her doggos and she kept them all super active! Really appreciated all the pictures and updates while I was gone. Would 100%book with her again!”

“Korie was amazing with Ollie! She was great to communicate with and gave Ollie so many snuggles while he was there. She also sent pics and updates throughout the stay which I really appreciate. Highly recommend!!”

“Jennifer and her family took amazing care of Finn. Also, their dog is super sweet and played well with my dog. Cant wait to have Jennifer sit Finn again soon!”

“Kris was great with Lacy. I like how she meet us before are stay to get to know us. She is so flexible my flight was late a she had no problem keeping Lacy a little longer. I will highly recommend her. I will be booking with her again.”

“Derek and Yoki did a wonderful job taking care of our dog (Captain). They provided great updates and some of the best photos I have seen of Captain. I would highly reccomend them for boarding services.”

“Super nice family and home with fenced yard. We needed someone on short notice due to a family emergency. Katie and Samuel offered to be flexible with our return date which we greatly appreciated. Juneau seemed to have done fine.”

Over 11 pet parents in Windsor have booked dog boarding
Windsor dog parents share their Rover experiences
This was our first boarding experience with Morgan and she was awesome. Our dog is a bit anxious and slow to warm up to people. It was clear from the start that Morgan understands dogs and can match their energy. She took great care of our Rosie and sent regular updates. It was great to enjoy our vacation without worrying about the dog. We also had some flight issues on the way home and Morgan was flexible and helpful.

Popular requests near you
Select a filter and find qualifying Windsor sitters!How Rover works

1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
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The median cost per night for dog boarding in Windsor is $45
Why Choose Rover?
Cashless payments
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 Windsor average 10 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Mar 2026, the median cost of dog boarding in Windsor is $45 per night, including service fees. Boarding your dog for one week typically costs $315. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Windsor dog boarding rates can be found as low as $26 to as high as $32 per night.
As of Mar 2026, 461 sitters provided dog boarding in Windsor. 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, 93% of Windsor dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Windsor have an average of 18 years of experience. Dog boarding sitters with repeat customers have an average of 10 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 Windsor.
Rover makes it easy to find Windsor 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 461 dog boarding sitters in Windsor on Rover, so you’re sure to find the perfect match for your dog! In Windsor, 87% of sitters offer daily exercise, 98% offer medication administration, and 98% 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.







