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.
“Korie took wonderful care of Dizzy! Her communication and updates were clear and she was flexible with pickup and drop off times. Would absolutely love for Dizzy to stay with Korie and Ozzy again.”

“We just completed our dogs 3rd stay at Sarah and Zach's house and we already have stay #4 booked. Our always have so much fun and get lots of outdoor playtime. We love the photo and video updates and especially enjoy knowing they are being so well cared for while we are away.”

“Jessica is the best sitter I have ever had on Rover!!! She took great care of my Mickey and provided lots of updates throughout each day. Will definitely book with her again, my dog had a great time with her and her dogs!!”

“I can't recommend Stephanie highly enough! She recently watched our dog, Hazel, and she was truly wonderful from start to finish. From the moment we dropped Hazel off, Stephanie provided excellent and frequent updates, including photos and videos, which really put our minds at ease. It was clear that Hazel was having a great time and felt completely comfortable in her care. Stephanie was incredibly reliable, easy to communicate with, and genuinely treated Hazel like her own family. Hazel came home tired, happy, and clearly well-loved. If you're looking for a trustworthy, loving, and professional sitter on Rover, book Stephanie—we certainly will be booking her again!”

“Paula was great communicating and even ended up spending the evenings with my pup on the sofa since she wasn't comfortable alone. She also gave necessary medication and kept track of everything as I had asked. She sent pictures and kept my dog happy and safe, would recommend and use again. Thank you!”

“Wonderful people, and excellent sitters to sit your dog. They know dogs. Theyve been doing ut a long time. They really care about what they do. There is always someone there. My pup got exercise and playmates and a good staycation . i will use them next time im in madison if theyre available.”

“Excellent! I really appreciated all the updates and photos from Stefanie. Great communication and flexible with drop off and pick up times. Will definitely use again in future.”

“Emily was the perfect sitter for Marley!! For a pup that tends to get a little anxious at first around other dogs, Emily immediately invited me to be there with her when she first met all the other dogs and got settled. It truly meant the world!! She also sent so many pictures and Marley was the happiest girl in all of them! Thank you Emily!!!”

“We had a great experience with Erik. We felt very comfortable leaving our first time foster dog with Erik's family. They met with us before to see if it was a good fit. He was very gracious in dealing with our situation. We would recommend Erik and would book with him again.”
“Kristin & Bruce were great hosts for our Corgi, JJ. This was our first time using Rover and they made the entire process easy, from drop off to pickup. They provided updates along with photos during his 30 hour stay. Would definitely book with them again and will recommend to others in the future. Thanks again for everything.”

“Pretzel has a great 2 week stay. Duane& Lauren took great care of him and he has lots of playtime and walks to keep him busy. Their place is warm and cozy even in the cold winter!”

“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!”

“This was the 2nd time Katie and Samuel’s family took care of Jarvis while we were away. We were very excited when they were available for these dates because Jarvis had a great time with them the first time. They did such an amazing job with him again and it really seemed like Jarvis felt right a home. They always send frequent updates and pictures which is really appreciated :)”


“This was Baylee's first boarding experience since I adopted her and she seems very happy and healthy. She loves walks and Erika provided multiple daily walks. Baylee's medication and feed requirements were met. I couldn't expect more than a happy dog!”

“Baba had a great time with Ellen! He was sad to be home and not have a big yard to run around, but he will return on our next trip. Ellen was great about sending photos of baba and letting us know how his day/night was.”

“Amanda was wonderful! She sent videos and pictures of Cece the entire time we were gone. I would highly recommend Amanda to anyone and plan to use her again in the future!”

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 11 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Jun 2026, 462 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 17 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 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 462 dog boarding sitters in Windsor on Rover, so you’re sure to find the perfect match for your dog! In Windsor, 89% of sitters offer daily exercise, 98% offer medication administration, and 93% 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.







