Pet Boarding Windsor

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

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Over 401
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.

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

Kaycee and Robert are the best! They took such good care of our little dog, who has never spent time away from us. They took him on walks, played with him, and kept him warm and safe. Our dog loved Tank (their dog) and the kids. He had a blast with this lovely family. They are kind and warm people who took excellent care of our dog. It is evident that they are expert dog owners who have fostered and trained many dogs. We will definitely book them next time we leave town. We highly recommend them!

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Hanan A.
Sitter Profile Image: Ellen S.
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Ellen S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
60 reviews
17 repeat clients
10 years of experience
Marshall, WI, 53559

Finny had a great time with Ellen and her family! He definitely did not want to come home when it was time to leave! Ellen was very communicative and sent updates and photos often, so I was very confident that Finny was having fun and was relaxed and happy.

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Kristine B.
Sitter Profile Image: Lindsey C.
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Lindsey C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
42 reviews
12 repeat clients
10 years of experience
Madison, WI, 53705

Lindsey was great with my dog! She made sure to update us with photos and activities throughout the days. Thank you Lindsey for showering my fur baby with love and lots of walks!💕

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Jennifer V.
Sitter Profile Image: Evelyn R.
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Evelyn R.
from
$28
per night
12 years of experience
De Forest, WI, 53532

About: I am a proud dog owner/parent who loves spending time with my two Frenchies. I love to have doggy friends come over and spend quality time playing, snuggling, and relaxing. I am currently doing consulting work from home in a part time basis and have a very flexible schedule. I can do doggy daycare during the week as well as some weekends. The house have a fenced backyard that is very safe for our dogs and our house is doggy proof. I have crates too if that is your preference, otherwise your pup will be inside the house with us.

Sitter Profile Image: Ryan & Martha M.
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Ryan & Martha M.
from
$41
per night
5.0 out of 5 stars
54 reviews
22 repeat clients
14 years of experience
Stone Meadows, Madison, WI, 53719

Martha and Ryan took great care of our dog Cosmo. They were great communicators and clearly enjoyed having a dog to take care of. The whole family was involved in his care and play, and Cosmo came home happy and tired. We look forward to having them take care of Cosmo again!

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Jeannette L.
Sitter Profile Image: Mary Z.
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Mary Z.
Star Sitter
from
$50
per night
5.0 out of 5 stars
18 reviews
9 repeat clients
10 years of experience
Regent, Madison, WI, 53726

Mary took our dog for our wedding weekend and she was great! Pugsy had a great time with her dog, going on a walk, and going to the dog park! She sent pictures and we did not worry about Pugsy at all! We will definitely book with Mary in the future!

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Jenna K.
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
31 reviews
7 repeat clients
15 years of experience
Carpenter-Ridgeway, Madison, WI, 53704

Thanks so much for always taking such great care of Ollie! I truly appreciate knowing he's in good hands, happy and snuggled while I'm away. ❤️

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Stephanie M.
Sitter Profile Image: Doua Song 'Jenny' & Darin K.
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Doua Song 'Jenny' & Darin K.
Star Sitter
from
$55
per night
5.0 out of 5 stars
26 reviews
7 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!

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Justina A.
Sitter Profile Image: Tessa S.
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Tessa S.
from
$35
per night
5.0 out of 5 stars
17 reviews
6 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!

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Kayla L.
Sitter Profile Image: Elizabeth S.
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Elizabeth S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
21 reviews
3 repeat clients
9 years of experience
Madison, WI, 53718

Such a great host family for our dog! She got loads of attention and exercise while she was there. Definitely returning and recommend highly.

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Theran M.
Sitter Profile Image: Amanda K.
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Amanda K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
190 reviews
62 repeat clients
20 years of experience
Cottage Grove, WI, 53527

Awesome people. Sent me a couple pictures of lulu during her stay, played with her, we had no worries all weekend. Definitely our go to for overnight boarding

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Alison S.
Sitter Profile Image: Shawn S.
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Shawn S.
from
$45
per night
5.0 out of 5 stars
8 reviews
1 repeat client
32 years of experience
McClellan Park, Madison, WI, 53718

Shawn was great! Sent picture updates and Caspian looked so happy and relaxed! He was super flexible and even worked with me as I needed to have a friend pick Cas for scheduling reasons. Thank you Shawn!

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Hannah T.
Sitter Profile Image: Yee Lam C.
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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!

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Mohini G.
Sitter Profile Image: Tanya & Hutch K.
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Tanya & Hutch K.
from
$40
per night
5.0 out of 5 stars
6 reviews
25 years of experience
Monona, WI, 53716

Tanya and Hutch could not have done a better job making Molly feel at home with them. You’re getting professional grade photos of your dog every day as well:) Thank you both so much:) Pete and Anne Jones

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Peter J.
Sitter Profile Image: Andrea P.
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Andrea P.
Star Sitter
from
$42
per night
5.0 out of 5 stars
18 reviews
4 repeat clients
1 year of experience
Sauk Creek, Madison, WI, 53717

We had a wonderful experience! This family took excellent care of our mini goldendoodle while we were on vacation—so kind, attentive, and thoughtful. They sent plenty of pictures and updates, which gave us total peace of mind and showed he was happy and having fun. Highly recommend!

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Nabeel Q.
Sitter Profile Image: Michelle S.
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Michelle S.
from
$50
per night
5.0 out of 5 stars
43 reviews
9 repeat clients
30 years of experience
Orchard Ridge Community, Madison, WI, 53711

This was Henry's second time staying with Michelle and her family, and he had a great time! I really appreciated the updates and pictures throughout his stay. I will definitely book with Michelle again :)

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Corinne H.
Sitter Profile Image: Hannah P.
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Hannah P.
from
$60
per night
5.0 out of 5 stars
9 reviews
4 repeat clients
18 years of experience
Vilas, Madison, WI, 53711

This is our second time leaving our dog with Hannah and her family and we couldn’t be happier. Our dog was so excited to see them, the ultimate sign of approval!

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Emma B.
Sitter Profile Image: Robert N.
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Robert N.
Star Sitter
from
$50
per night
5.0 out of 5 stars
202 reviews
69 repeat clients
20 years of experience
Orchard Ridge Community, Madison, WI, 53711

Robert was amazing! Lots of updates, great communication, and not a doubt in my mind that my dog was being taken care of well! I would absolutely let him watch Thor again!

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Daria D.
Sitter Profile Image: Cleda W.
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Cleda W.
Star Sitter
from
$60
per night
5.0 out of 5 stars
223 reviews
88 repeat clients
11 years of experience
Spring Harbor, Madison, WI, 53705

Thank you Camp Cleda for pet sitting Pumba and Snooki. Snooki came home happy to see me (unlike her last sitter experience). Thank you for the pic updates & for being so responsive. We appreciate your patience with our anxious & sassy senior dogs too, and look forward to boarding with you again. ☺️

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Doua Song 'Jenny' & Darin K.
Sitter Profile Image: Elena "Sofi" R.
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Elena "Sofi" R.
Star Sitter
from
$45
per night
5.0 out of 5 stars
44 reviews
12 repeat clients
5 years of experience
Capitol, Madison, WI, 53715

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!!

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

Pet parents share their Rover experiences - Windsor

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5.0 out of 5 stars

Once again, Toni did a great job with Augie while we were on vacation. She took him to the dog park almost every day and sent us daily updates with photos. Augie came home happy and healthy.

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Philip B.
Boarding
5.0 out of 5 stars

Gwen was amazing with our puppy Otto. He is a higher needs puppy and we felt very safe leaving him in her care! Great communication! Lots of pictures! Would definitely bring him back for another stay in the future!

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Courtney N.
Boarding
5.0 out of 5 stars

As always, I can tell that Rucci loves her time with Becca. Becca is a great communicator when booking and about Rucci’s time with her.

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Angela S.
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.

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Julia L.
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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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
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Popular requests for pet boarding - Windsor

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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 $36.63 per night (as of August 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 450 sitters on Rover for Pet Boarding in Windsor. About 93% 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.

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