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: Sarah M.
Verified Enhanced Background Check
Sarah M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
105 reviews
13 repeat clients
35 years of experience
Deforest, WI, 53532

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!

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

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.

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Mizzy R.
Sitter Profile Image: Ronalisa E.
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Ronalisa E.
Star Sitter
from
$30
per night
5.0 out of 5 stars
22 reviews
8 repeat clients
6 years of experience
Madison, WI, 53704

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.

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Marceilla T.
Sitter Profile Image: Gilian S.
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Gilian S.
Star Sitter
from
$48
per night
5.0 out of 5 stars
223 reviews
58 repeat clients
8 years of experience
Sun prairie, WI, 53590

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.

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Susana S.
Sitter Profile Image: Yee Lam C.
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Yee Lam C.
from
$45
per night
5.0 out of 5 stars
8 reviews
1 repeat client
20 years of experience
Sun Prairie, WI, 53590

Yee Lam was great and Finn had a great time! She took him for multiple walks a day and would send photos. And would give me updates on how he did!

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Mohini G.
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
261 reviews
144 repeat clients
20 years of experience
Sun Prairie, WI, 53590

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.

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Adam B.
Sitter Profile Image: Rebecca B.
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Rebecca B.
from
$56
per night
5.0 out of 5 stars
29 reviews
4 repeat clients
20 years of experience
Deforest, WI, 53532

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 :)

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Becky L.
Sitter Profile Image: Joan F.
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Joan F.
Star Sitter
from
$40
per night
5.0 out of 5 stars
154 reviews
44 repeat clients
18 years of experience
Eastmorland, Madison, WI, 53714

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!

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Ivy M.
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
71 reviews
21 repeat clients
30 years of experience
Ridgewood, Madison, WI, 53704

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!

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Russhell C.
Sitter Profile Image: Kaycee & Robert R.
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Kaycee & Robert R.
Star Sitter
from
$30
per night
5.0 out of 5 stars
29 reviews
4 repeat clients
13 years of experience
Heritage Heights, Madison, WI, 53714

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.

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Elizabeth J.
Sitter Profile Image: Erik R.
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Erik R.
from
$30
per night
4.9 out of 5 stars
29 reviews
11 repeat clients
15 years of experience
Sun Prairie, WI, 53590

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.

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Brian & Jessie B.
Sitter Profile Image: Alexander & Hannah K.
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Alexander & Hannah K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
24 reviews
4 repeat clients
15 years of experience
Carpenter-Ridgeway, Madison, WI, 53704

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.

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Kennedy Z.
Sitter Profile Image: Lindsey C.
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Lindsey C.
Star Sitter
from
$45
per night
5.0 out of 5 stars
31 reviews
8 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: Jessica M.
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Jessica M.
from
$40
per night
5.0 out of 5 stars
20 reviews
2 repeat clients
25 years of experience
Rolling Meadows, Madison, WI, 53714

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!

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Emily G.
Sitter Profile Image: Korie L.
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Korie L.
Star Sitter
from
$45
per night
5.0 out of 5 stars
12 reviews
3 repeat clients
20 years of experience
Madison, WI, 53718

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!!

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Angi K.
Sitter Profile Image: Jennifer & Phil Z.
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Jennifer & Phil Z.
from
$35
per night
5.0 out of 5 stars
9 reviews
1 repeat client
5 years of experience
Dudgeon-Monroe, Madison, WI, 53711

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!

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Heather A.
Sitter Profile Image: Kris A.
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Kris A.
from
$40
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
16 years of experience
DeForest, WI, 53532

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.

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Mary P.
Sitter Profile Image: Derek & Yoki S.
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Derek & Yoki S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
61 reviews
19 repeat clients
7 years of experience
Lake Edge, Madison, WI, 53716

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.

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Chris B.
Sitter Profile Image: Emily L.
Verified Enhanced Background Check
Emily L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
91 reviews
27 repeat clients
20 years of experience
Mc Farland, WI, 53558

Thank you so much! Emily watch my Marshal late notice absolutely put my mind at ease. They sent me pictures every day and loved on him more than when he is home!

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Jonathan S.
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
24 reviews
11 repeat clients
20 years of experience
MIDDLETON, WI, 53562

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.

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J&S W.
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Over 11
pet parents in Windsor have booked dog boarding

Windsor dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

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 :)

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Becky L.
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

Toni is a very experienced and caring dog sitter. She communicated great and handled several challenging issues that came up with grace and excellent problem solving. I would recommend her without hesitation!

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Sabrina C.
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
5.0 out of 5 stars

We love Paula! She cares for our pup so well and takes him on so many walks. We feel very safe and comfortable when Lou is in her care. Which is such a blessing!

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Julia L.
Boarding
5.0 out of 5 stars

Gwen is a wonderful dog sitter! She is friendly, kind, energetic and very responsive with updates and pictures which was so nice! She took good care of our dog while we were away for 6-days. We will definitely rebook with Gwen 😁

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Christina A.
Boarding
5.0 out of 5 stars

Kendall was so lovely. She kept us informed on how Marv was going and shared a ton of pictures. I would 1000% use Kendall again.

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Brittney R.
Boarding
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Find pet care near you

How Rover works

  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

    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.

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 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.