Dog Boarding in Windsor, WI

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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.

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Sitter Profile Image: Edith S.
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Edith S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
70 reviews
25 repeat clients
20 years of experience
Waunakee, WI, 53597

My dog seems to enjoy staying with Edith and her pack. Edith keeps me updated with pictures everyday. I feel very comfortable leaving her with Edith.

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Steve G.
Sitter Profile Image: Korie L.
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Korie L.
Star Sitter
from
$40
per night
5.0 out of 5 stars
16 reviews
7 repeat clients
20 years of experience
Madison, WI, 53718

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.

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Carol P.
Sitter Profile Image: Sarah M.
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Sarah M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
121 reviews
17 repeat clients
35 years of experience
Deforest, WI, 53532

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.

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Lisa W.
Sitter Profile Image: Jessica M.
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Jessica M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
36 reviews
8 repeat clients
25 years of experience
Rolling Meadows, Madison, WI, 53714

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!!

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Allison M.
Sitter Profile Image: Stephanie E.
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Stephanie E.
Star Sitter
from
$42
per night
5.0 out of 5 stars
22 reviews
6 repeat clients
18 years of experience
Madison, WI, 53704

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!

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Michael K.
Sitter Profile Image: Regine T.
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Regine T.
from
$40
per night
5.0 out of 5 stars
6 reviews
1 repeat client
5 years of experience
Sun Prairie, WI, 53590

Wonderful dog sitter! Sent photos daily and gave updates!!! Loved on my pup and treated him like one of their own! Will definitely use Regine again!!!

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Joelle T.
Sitter Profile Image: Paula R.
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Paula R.
Star Sitter
from
$40
per night
5.0 out of 5 stars
87 reviews
27 repeat clients
5 years of experience
Southeast, DeForest, WI, 53532

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!

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Amy A.
Sitter Profile Image: LAVAL [VAL] S.
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LAVAL [VAL] S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
272 reviews
148 repeat clients
30 years of experience
Sun Prairie, WI, 53590

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.

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Ryan Z.
Sitter Profile Image: Stefanie B.
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Stefanie B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
63 reviews
20 repeat clients
12 years of experience
Middleton, WI, 53562

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.

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Sarah W.
Sitter Profile Image: Emily L.
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Emily L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
110 reviews
35 repeat clients
20 years of experience
Mc Farland, WI, 53558

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!!!

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Audrey M.
Sitter Profile Image: Erik R.
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Erik R.
from
$30
per night
4.9 out of 5 stars
33 reviews
12 repeat clients
15 years of experience
Sun Prairie, WI, 53590

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.

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Julie t.
Sitter Profile Image: Kristin & Bruce M.
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Kristin & Bruce M.
Star Sitter
from
$35
per night
5.0 out of 5 stars
100 reviews
29 repeat clients
2 years of experience
Madison, WI, 53719

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.

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Terry F.
Sitter Profile Image: Duane & Lauren S.
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Duane & Lauren S.
Star Sitter
from
$20
per night
5.0 out of 5 stars
78 reviews
24 repeat clients
30 years of experience
Ridgewood, Madison, WI, 53704

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!

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Brian P.
Sitter Profile Image: Lindsey C.
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Lindsey C.
Star Sitter
from
$45
per night
5.0 out of 5 stars
39 reviews
9 repeat clients
10 years of experience
Madison, WI, 53705

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!

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Richard M.
Sitter Profile Image: Katie & Samuel W.
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Katie & Samuel W.
Star Sitter
from
$45
per night
5.0 out of 5 stars
29 reviews
12 repeat clients
20 years of experience
MIDDLETON, WI, 53562

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 :)

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Justin L.
Sitter Profile Image: Erika M.
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Erika M.
from
$43
per night
4.9 out of 5 stars
163 reviews
77 repeat clients
13 years of experience
Sun Prairie, WI, 53590

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!

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Patti P.
Sitter Profile Image: Ellen S.
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Ellen S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
56 reviews
16 repeat clients
10 years of experience
Marshall, WI, 53559

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.

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Samm S.
Sitter Profile Image: Amanda K.
Verified Background Check
Amanda K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
184 reviews
59 repeat clients
20 years of experience
Cottage Grove, WI, 53527

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!

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Jennifer W.
Sitter Profile Image: Elena "Sofi" R.
Verified Enhanced Background Check
Elena "Sofi" R.
Star Sitter
from
$45
per night
5.0 out of 5 stars
37 reviews
11 repeat clients
5 years of experience
Capitol, Madison, WI, 53715

Sofi was great! She frequently shared photos of Ollie during his time with her and communicated how he was doing while staying with her and her dog.

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Susan S.
Sitter Profile Image: Kris A.
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Kris A.
from
$40
per night
5.0 out of 5 stars
13 reviews
4 repeat clients
16 years of experience
DeForest, WI, 53532

Kris was absolutely fantastic. I felt very comfortable leaving Cokes with Kris and her household. Would not hesitate to use again. Thank you so much!

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Richard M.
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Windsor dog parents share their Rover experiences

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5.0 out of 5 stars

My dog loved her time at Becca’s house! I could tell that Rucci felt at home there when I dropped her off. I always try to book Becca first when I need a sitter.

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Angela S.
Boarding
5.0 out of 5 stars

Paula was great to work with again and George seemed to have a fun time getting plenty odd walls and pets :)

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Monica P.
Boarding
5.0 out of 5 stars

Ollie had such a great time with Toni. We were updated with pictures and notes from her while we were away and he looked very well taken care of. Thanks so much, Toni!

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Erin W.
Boarding
5.0 out of 5 stars

Kris is great! Wagyu loves having a family and a home to go to and I love getting updates on what he's up to while knowing he's in great hands :)

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Madeleine S.
Boarding
5.0 out of 5 stars

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.

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Cindy H.
Boarding
5.0 out of 5 stars

I am so thankful for Maria and Bryan. They showed so much patience to Aza who is a very sensitive dog. They also kept me well informed on how she was doing.

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Yolibeth R.
Boarding
5.0 out of 5 stars

Susan and Molly are great! Our dog loves it there! They take great care of him and do a wonderful job keeping us informed on how things are going. Highly recommend!

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Lori S.
Boarding
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  1. 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. 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. 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

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  • 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

If you’re searching for a Windsor dog boarding sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

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.