Pet Boarding Windsor

Find a loving Windsor pet sitter to watch your cat or dog overnight at your sitter’s home.

End Date
Search

Over 402
pet parents in Windsor have booked pet boarding

Windsor, Find top rated pet boarding

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Margaret L.
Verified Enhanced Background Check
Margaret L.
Star Sitter
from
$46
per night
5.0 out of 5 stars
31 reviews
8 repeat clients
10 years of experience
Emerson East, Madison, WI, 53704

Margaret was great with our dog, Comet! She sent photos and updates and Comet seemed very happy both in the photos and when we got back. I would highly recommend booking Margaret and we will try and book her again in the future!

Profile image
Katy J.
Sitter Profile Image: Katie & Samuel W.
Verified Enhanced Background Check
Katie & Samuel W.
Star Sitter
from
$45
per night
5.0 out of 5 stars
30 reviews
13 repeat clients
20 years of experience
MIDDLETON, WI, 53562

Thank you for taking such great care of our dog! We appreciated the picture, video, and text updates and that you included Teddy in your activities. You took great care of him! Will schedule again.

Profile image
Stephen B.
Sitter Profile Image: Amanda K.
Verified Background Check
Amanda K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
188 reviews
60 repeat clients
20 years of experience
Cottage Grove, WI, 53527

I couldn’t be happier with Rosie’s stay! Amanda sent pictures and Rosie was clearly having a wonderful time and fit right in. When I picked her up she was tired from playing and very happy. Rosie will definitely be a frequent visitor!

Profile image
Susan V.
Sitter Profile Image: Mattison & Eli H.
Verified Enhanced Background Check
Mattison & Eli H.
from
$50
per night
5.0 out of 5 stars
4 reviews
15 years of experience
Madison, WI, 53718

Great communication for booking, through their stay, and when we needed to adjust our pick up time. We received pictures of our ladies several times, which brightened our day and helped us feel at ease when we were away. They were very attentive to the different food and medication needs our ladies have. We will definitely use them again for future boarding.

Profile image
Cole O.
Sitter Profile Image: Doua Song 'Jenny' & Darin K.
Verified Enhanced Background Check
Doua Song 'Jenny' & Darin K.
Star Sitter
from
$55
per night
5.0 out of 5 stars
24 reviews
6 repeat clients
15 years of experience
Stone Meadows, Madison, WI, 53719

Our quirky rescue pup was so well taken care of while we were away! In every update we got it was clear that our dog was feeling more and more comfortable and was left in good hands. We will definitely book again!

Profile image
Justina A.
Sitter Profile Image: Alexander & Hannah K.
Verified Enhanced Background Check
Alexander & Hannah K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
31 reviews
7 repeat clients
15 years of experience
Carpenter-Ridgeway, Madison, WI, 53704

Alex and Hannah gave lots of TLC with nice walks in the wooded trails nearby. They were extremely accommodating when we arrived late and then had a delayed return. Thanks!

Profile image
Mary R.
Sitter Profile Image: Yee Lam C.
Verified Enhanced Background Check
Yee Lam C.
Star Sitter
from
$45
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
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!

Profile image
Mohini G.
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
43 reviews
12 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.

Profile image
Susan S.
Sitter Profile Image: Juan P.
Verified Enhanced Background Check
Juan P.
from
$30
per night
4.6 out of 5 stars
13 reviews
4 repeat clients
8 years of experience
Leopold, Fitchburg, WI, 53713

I just picked up Lily at the arranged pickup time of 10 am and she was looking better than she had in a long time. She was happy and energetic. Thanks Juan for your professionalism and taking such great care of our girl. I will definitely book you again soon🤩

Profile image
Batenga O.
Sitter Profile Image: Kaycee & Robert R.
Verified Enhanced Background Check
Kaycee & Robert R.
Star Sitter
from
$35
per night
5.0 out of 5 stars
34 reviews
4 repeat clients
16 years of experience
Heritage Heights, Madison, WI, 53714

Last minute booking and sitter was super accommodating! Kept me posted with pics and videos. I felt super comfortable and that my pup was in good hands as soon as I walked in the door! Highly highly recommend!

Profile image
Jessica V.
Sitter Profile Image: Andrea P.
Verified Enhanced Background Check
Andrea P.
Star Sitter
from
$44
per night
5.0 out of 5 stars
17 reviews
4 repeat clients
1 year of experience
Sauk Creek, Madison, WI, 53717

Very friendly and dependable. Timely communication, and great pictures and updates during the stay. Confident that Louie got lots of attention, exercise, doggy socialization, and love.

Profile image
Matt S.
Sitter Profile Image: Suellen A.
Verified Enhanced Background Check
Suellen A.
Star Sitter
from
$55
per night
5.0 out of 5 stars
70 reviews
24 repeat clients
35 years of experience
Schenk-Atwood, Madison, WI, 53704

Suellen was amazing with Kanye! From the moment we connected, communication was easy and genuine. She kept us updated and made us feel completely at ease while we were away. The best part was seeing how happy and comfortable Kanye was with her you can tell she truly cares and connects with the pets she watches. We loved getting updates and seeing him so relaxed and joyful. Highly recommend Suellen we will absolutely book with her again!

Profile image
Alicia W.
Sitter Profile Image: Alicia D.
Verified Enhanced Background Check
Alicia D.
Star Sitter
from
$55
per night
5.0 out of 5 stars
96 reviews
25 repeat clients
10 years of experience
Worthington Park, Madison, WI, 53714

Alicia was great! She was very responsive and accommodating. The boys seemed really happy when we picked them up. I would definitely trust her to watch them again

Profile image
Annika S.
Sitter Profile Image: David R.
Verified Enhanced Background Check
David R.
Star Sitter
from
$45
per night
5.0 out of 5 stars
16 reviews
8 repeat clients
15 years of experience
Madison, WI, 53705

Excellent care for Judge. Had no issues whatsoever. Prompt communication and daily updates during the stay. Will definitely recommend and book again.

Profile image
Ushmal R.
Sitter Profile Image: Beatrice L.
Verified Enhanced Background Check
Beatrice L.
from
$40
per night
5.0 out of 5 stars
6 reviews
1 repeat client
2 years of experience
Bay Creek, Madison, WI, 53715

Beatrice did a great job watching over Chopa :) She sent messages and pictures to provide updates during the boarding which was great! I would definitely reach out to her again when we need boarding service again

Profile image
Tracy K.
Sitter Profile Image: Robert N.
Verified Enhanced Background Check
Robert N.
Star Sitter
from
$50
per night
5.0 out of 5 stars
197 reviews
66 repeat clients
20 years of experience
Orchard Ridge Community, Madison, WI, 53711

Maui had a wonderful time with Robert. Robert is very good about sending updates and photos of Maui. I got multiple messages per day ensuring me that Maui was doing well. I know Maui can’t wait to go visit Robert again soon.

Profile image
Spencer M.
Sitter Profile Image: Lorelei & Kayla E.
Verified Background Check
Lorelei & Kayla E.
Star Sitter
from
$45
per night
5.0 out of 5 stars
258 reviews
114 repeat clients
35 years of experience
Madison, WI, 53713

Russia had a great time with Kayla. She went to the dog park and even got to go in the kitty pool. Russia came back exhausted which is a great sign that she had a fun filled stay. Kayla was very responsive to my messages and was very easy to work with.

Profile image
Becky S.
Sitter Profile Image: Tessa S.
Verified Enhanced Background Check
Tessa S.
from
$35
per night
5.0 out of 5 stars
17 reviews
5 repeat clients
7 years of experience
Fitchburg, WI, 53711

Tessa is always just the best! She cares and loves Rena like her own - taking her in the best walks and adventures with her dog Tennessee. We can’t thank Tessa enough!

Profile image
Kayla L.
Sitter Profile Image: Tonisha A.
Verified Background Check
Tonisha A.
Star Sitter
from
$63
per night
5.0 out of 5 stars
50 reviews
13 repeat clients
30 years of experience
Sun Prairie, WI, 53590

Tonisha was wonderful! Ollie was able to meet Tonisha and her dog before booking to determine compatibility. Tonisha sent frequent photos of Ollie to showcase that he was doing well in her care. Ollie and I would be fortunate to have Tonisha care for Ollie again.

Profile image
Susan S.
Sitter Profile Image: Cleda W.
Verified Background Check
Cleda W.
Star Sitter
from
$60
per night
5.0 out of 5 stars
223 reviews
87 repeat clients
11 years of experience
Spring Harbor, Madison, WI, 53705

Cleda was great with our pups! Easy drop off and oick up. She kept us updated with photos and texts all weekend and the boys came home happy and tired! We will definitely use Cleda again.

Profile image
Monica C.
1 / 1
View more

The median cost per night for pet boarding in Windsor is $45

Pet parents share their Rover experiences - Windsor

1 / 1
5.0 out of 5 stars

I was so thankful for frequent updates during our dogs' stay. They seemed very comfortable and well cared for when we picked them up.

Profile image
Kelsey H.
Boarding
5.0 out of 5 stars

We call Paula’s our dogs “retreat.” He loves it there and always seems so calm when we drop him off. She cares for your pet like her own and I’m so thankful our dog can stay with her.

Profile image
Julia L.
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!

Profile image
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 :)

Profile image
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.

Profile image
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.

Profile image
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!

Profile image
Lori S.
Boarding
1 / 1
Find pet care near you

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer pet boarding
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for pet boarding - Windsor

Select a filter and find qualifying sitters offering pet boarding.

Sitters in Windsor average 11
repeat pet boarding clients

FAQs for Boarding - Windsor

Frequently asked questions about Rover

The average cost for Pet Boarding in Windsor on Rover is $36.09 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Pet Boarding easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Pet Boarding. For more information on service fees, click here .

There are 472 sitters on Rover for Pet Boarding in Windsor. About 92% of Windsor sitters can respond to requests in under 60 minutes. Whether you’re planning ahead for holidays, need last-minute care, or need same-day coverage for an urgent trip, you can message multiple sitters at once to find available care.

Once you find the right match, you can arrange a Meet & Greet to ensure they are a perfect fit for your pet’s personality before confirming.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in WI ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies. Cats may be required to have Feline Viral Rhinotracheitis and Rabies up to date.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

Emergency support is available by phone or email in English 24/7. When an incident occurs, we recommend that sitters contact our Trust & Safety team immediately so that they can connect your sitter with a board-certified veterinarian or offer other resources to help.

If a sitter needs to cancel at the last minute, Rover’s reservation protection means our team will work with you to find a suitable replacement as quickly as possible.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge