Dog Boarding in Windsor, WI
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Top rated Windsor dog boarders

“Edith was great with our puppy Artemis! We were able to meet beforehand for a short notice meet and greet before the holidays. Artemis got along really well with her two dogs and it seemed like he was having a lot of fun throughout the day- he came back exhausted and happy to see us after a couple of weeks, but we could tell that he was well taken care of. Edith sent frequent picture updates, and we felt like he was in good hands the whole time. I would definitely book Artemis here again in the future!”


“Gilian was an amazing choice for boarding my dog! First we did a meet and greet at a local dog park, and then welcomed my dog to her home for a week+ of boarding. My anxious pup felt comfortable here after a couple days, and was well cared for. We can't do boarding kennels because of my dog's anxiety, so I'm so glad we found this service! I got updates daily about activities and behavior, as well as photos and videos! Gilian is knowledgeable handling anxious dogs, and she has good techniques on introducing dogs to new environments, dogs and people to help ease anxiety. I highly recommend Gilian!”


“Val took great care of my two dogs. He was very responsive, flexible with drop off/pick up times, and sent updates with pictures throughout their stay. I would definitely use him again in the future.”


“Bob is so wonderful, I couldn’t have asked for a better sitter for Joey! He was incredibly kind and funny and sent lots of photos and updates throughout the long weekend. Bob was also responsive to any messages and everything was so easy to coordinate, from the meet and greet, to drop off, to pick up, which we were able to time with our flight arrival perfectly. Joey was a very happy pup when I picked him up and we would love to board with Bob again!”


“Kristin was great with my dog Lacy. I would highly recommend her. She sent me pictures and made sure I now that Lacy was doing great. I will be using her again next time I travel.”


“Duane and Lauren are always so accommodating and flexible when we book with them! Our pup is always exciting to stay with them and it makes me happy to know she likes to be there! Thank you so much Duane and Lauren for always taking care of Stormi!”


“Joan is the best. She sent me daily updates and pictures of my baby. I hate being away from Randall, as many pet owners do, but it definitely gave me peace of mind having him with Joan. I knew he was being well taken care of and having a good time! Joan was responsive and easy to work with as well!”


“Kaycee and Robert did a great job with our little puppy Milton. We loved that Milton could play with their kids, run around in the backyard with their dog, and feel at home. He’s a handful and came home happy!”


“Excellent host! They send daily pictures and updates. My dogs looked so happy being in their home and backyard. Great communication and very flexible and accommodating.”


“Amazing people who love and care for my pup while he is with them - they also send the cutest pictures and updates! They were also super understanding when I got stuck in traffic on the way to pick my dog up.”


“Toni was amazing! This was our first time leaving our puppy with a sitter and we were so impressed! Annie clearly had a ton of fun, she came back absolutely pooped! Toni also sent us lots of updates and pictures :)”


“Amanda and her family are like a second family to our Rosie! Amanda is flexible, easy to communicate with and provides a great place for our pup when we’re out of town.”


“Anne kept me informed throughout Tut’s stay with updates on how he was doing and what they were up to. Tut had a great time on all the walks Anne took him on and enjoyed Tina as a playmate.”


“My mini poodle absolutely LOVES going to Camp Laura! Penny stayed with Laura recently for several days, and Laura took such amazing care of her. Penny got to walk and go to the dog park daily, play with Laura's pets and sleep in comfort each night. I never worry when Penny stays with Laura because Laura is so kind and caring. We will enlist Laura again when we need a safe and happy place for Penny! Thank you, Laura!”


“Kristin & family provided attentive & thorough care for our energetic puppy! Receiving regular updates was appreciated, as was their clear & responsive communication.”


“I could not ask for a better care provider for my Maltese Ollie, who has been cared for by only family members until recently! Hope went above and beyond to ensure that Ollie was comfortable while I was away. She invited Ollie and me to her home before committing to caring for Ollie. She was honest in sharing his daily joys and stressors, which was refreshing! She also provided suggestions to improve Ollie's comfort the next time I am away - too awesome!”


“Al and Hannah were phenomenal! They were very responsive and sent a lot of updates through my dog's stay. It made me feel very comfortable leaving Cas with them, and I absolutely will again if the need arises. Highly recommend!”


“Michelle is amazing! She was so communicative and provided lots of pictures. Good updates and very receptive. She took the time to really listen to my dogs backstory. I knew my dog was being well taken care of and I would absolutely have her watch him again!”

Loving dog boarding sitters in your neighborhood
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Edith S.Star Sitter

“Edith was great with our puppy Artemis! We were able to meet beforehand for a short notice meet and greet before the holidays. Artemis got along really well with her two dogs and it seemed like he was having a lot of fun throughout the day- he came back exhausted and happy to see us after a couple of weeks, but we could tell that he was well taken care of. Edith sent frequent picture updates, and we felt like he was in good hands the whole time. I would definitely book Artemis here again in the future!”


Gilian S.Star Sitter

“Gilian was an amazing choice for boarding my dog! First we did a meet and greet at a local dog park, and then welcomed my dog to her home for a week+ of boarding. My anxious pup felt comfortable here after a couple days, and was well cared for. We can't do boarding kennels because of my dog's anxiety, so I'm so glad we found this service! I got updates daily about activities and behavior, as well as photos and videos! Gilian is knowledgeable handling anxious dogs, and she has good techniques on introducing dogs to new environments, dogs and people to help ease anxiety. I highly recommend Gilian!”


LAVAL [VAL] S.
Star Sitter


“Val took great care of my two dogs. He was very responsive, flexible with drop off/pick up times, and sent updates with pictures throughout their stay. I would definitely use him again in the future.”


Robert L.
Star Sitter


“Bob is so wonderful, I couldn’t have asked for a better sitter for Joey! He was incredibly kind and funny and sent lots of photos and updates throughout the long weekend. Bob was also responsive to any messages and everything was so easy to coordinate, from the meet and greet, to drop off, to pick up, which we were able to time with our flight arrival perfectly. Joey was a very happy pup when I picked him up and we would love to board with Bob again!”


Kristin K.Star Sitter

“Kristin was great with my dog Lacy. I would highly recommend her. She sent me pictures and made sure I now that Lacy was doing great. I will be using her again next time I travel.”


Paula R.Star Sitter

“Paula takes very good care of our Sadie. Sadie is happy to see Paula when being dropped off so I know that’s true. They go on walks and Paula sends pictures.”


Duane & Lauren S.Star Sitter

“Duane and Lauren are always so accommodating and flexible when we book with them! Our pup is always exciting to stay with them and it makes me happy to know she likes to be there! Thank you so much Duane and Lauren for always taking care of Stormi!”


Joan F.Star Sitter

“Joan is the best. She sent me daily updates and pictures of my baby. I hate being away from Randall, as many pet owners do, but it definitely gave me peace of mind having him with Joan. I knew he was being well taken care of and having a good time! Joan was responsive and easy to work with as well!”


Kaycee & Robert R.

“Kaycee and Robert did a great job with our little puppy Milton. We loved that Milton could play with their kids, run around in the backyard with their dog, and feel at home. He’s a handful and came home happy!”


Yoki & Derek Z.Star Sitter

“Excellent host! They send daily pictures and updates. My dogs looked so happy being in their home and backyard. Great communication and very flexible and accommodating.”


Autumn H.Star Sitter

“Great communication, friendly and has helped us in a pinch multiple times!”


Katie & Samuel W.Star Sitter

“Amazing people who love and care for my pup while he is with them - they also send the cutest pictures and updates! They were also super understanding when I got stuck in traffic on the way to pick my dog up.”


Toni S.

“Toni was amazing! This was our first time leaving our puppy with a sitter and we were so impressed! Annie clearly had a ton of fun, she came back absolutely pooped! Toni also sent us lots of updates and pictures :)”


Amanda K.Star Sitter

“Amanda and her family are like a second family to our Rosie! Amanda is flexible, easy to communicate with and provides a great place for our pup when we’re out of town.”


Anne S.Star Sitter

“Anne kept me informed throughout Tut’s stay with updates on how he was doing and what they were up to. Tut had a great time on all the walks Anne took him on and enjoyed Tina as a playmate.”


Laura S.Star Sitter

“My mini poodle absolutely LOVES going to Camp Laura! Penny stayed with Laura recently for several days, and Laura took such amazing care of her. Penny got to walk and go to the dog park daily, play with Laura's pets and sleep in comfort each night. I never worry when Penny stays with Laura because Laura is so kind and caring. We will enlist Laura again when we need a safe and happy place for Penny! Thank you, Laura!”


Kristin & Bruce M.Star Sitter

“Kristin & family provided attentive & thorough care for our energetic puppy! Receiving regular updates was appreciated, as was their clear & responsive communication.”


Hope R.

“I could not ask for a better care provider for my Maltese Ollie, who has been cared for by only family members until recently! Hope went above and beyond to ensure that Ollie was comfortable while I was away. She invited Ollie and me to her home before committing to caring for Ollie. She was honest in sharing his daily joys and stressors, which was refreshing! She also provided suggestions to improve Ollie's comfort the next time I am away - too awesome!”


Alexander & Hannah K.

“Al and Hannah were phenomenal! They were very responsive and sent a lot of updates through my dog's stay. It made me feel very comfortable leaving Cas with them, and I absolutely will again if the need arises. Highly recommend!”


Michelle F.

“Michelle is amazing! She was so communicative and provided lots of pictures. Good updates and very receptive. She took the time to really listen to my dogs backstory. I knew my dog was being well taken care of and I would absolutely have her watch him again!”
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 dogs2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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.
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 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 Aug 2025, 433 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 433 dog boarding sitters in Windsor on Rover, so you’re sure to find the perfect match for your dog! In Windsor, 91% 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.
