Dog Boarding in Windsor, WI
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Top rated Windsor dog boarders
“Edith was wonderful,she kept me updated everyday with pictures and text messages. We were gone for ten days and I could enjoy my trip knowing she was taking care of and giving the best care to my two dogs. It’s great to feel free to travel and know that your pet is well taken care of. We look forward to working with Edith again and we’ll recommend her to our friends.”
“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.”
“Finny had a blast! I got updates every day and I could see how happy and content he was while I was on vacation. I was very comfortable knowing he was safe and having a great time, and when he got home he was good and tired. Thank you so much! I would be super happy to bring him back and would highly recommend.”
“Absolutely fantastic! Gave Odin so love, attention, and exercise! Gave updates throughout the week. Could not have asked for anyone better to care for my dog while I was away!”
“Jessica was wonderful and super friendly. My dog Bell stayed for a few days and we got the cutest picture updates. Her dogs are so well behaved and Bell was so happy she had friends to vacation with. She came home and slept the rest of the night! Would book again and will recommend her to others!”
“Paula is amazing!! She accommodated my 1-year-old terrier Teo for about 10 days. When I pick Teo up I can instantly tell he’s been happily taken great care of and has enjoyed Paula’s accompany. I couldn’t appreciate Paula more.”
![Sitter Profile Image: LAVAL [VAL] S.](https://www.rover.com/cf-image-cdn/remote/images/people/3gmOZo1A/czdjwirazm/original?width=200&height=200&quality=70&fit=cover)
“Val and his wife were absolutely wonderful with Logan! They gave him so much love and attention, and I felt completely at ease while we were away. I really appreciated the updates and could tell Logan was happy and well cared for. I highly recommend them and would definitely book again!”
“Stephanie was an amazing sitter. She messaged me daily with pictures too. Walks, playtime and belly rubs were a daily occurrence with Mack. I was afraid he wouldn’t want to come back home. 😊”
“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!”
“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.”
“6/5 stars! We felt so lucky to have Kristin, Bruce and their kiddos caring for walnut for almost 2 weeks… we got several photos and updates and they truly seemed to enjoy having the little guy. He came back to us relaxed and happy and we are so appreciative!”
“Duane and Lauren were wonderful to work with and took great care of our two dogs!!! Their communication was terrific and they were very flexible. We would love to have our dogs stay with them again!!”
“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 :)”
“Amanda and her family were extremely accommodating and took care of my dog like he was their own. It was my first time using the app and I was nervous but she put that at ease with updates and pictures. Would definitely book again!”
“Ellen did a wonderful job caring for our dog. She provided updates and pictures throughout the stay, and was extremely prompt and responsive. Our dog had a blast playing with her dogs, and enjoyed her large fenced in yard—I think it was hard to leave his new friends to come home!”
“Sofi took incredible care of our girl! She was always responsive and sent us frequent updates where I could see how happy Kiwi was. She is very knowledgeable about pet care and I would trust her with Kiwi anytime! Thank you again for giving so much love to Kiwi!!”
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
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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.
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