Pet Boarding Windsor

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

Pick-Up
Search

Over 404
pet parents in Windsor have booked pet boarding

Windsor, Find top rated pet boarding

1 / 1
Sitter Profile Image: Amanda K.
Verified Background Check
Amanda K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
190 reviews
63 repeat clients
20 years of experience
Cottage Grove, WI, 53527

Our dog simba had a great stay with Amanda and her family. We loved getting updates and pictures of how he’s doing. Definitely will be using her again next time we’re away. Thank you!

Profile image
Marta M.
Sitter Profile Image: Ellen S.
Verified Enhanced Background Check
Ellen S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
63 reviews
18 repeat clients
10 years of experience
Marshall, WI, 53559

Ellen took terrific care of our old girl! She went above and beyond helping her get through a few health/diet issues that came up during the stay. Very responsive and helpful updates throughout the stay. Would recommend Ellen to anyone looking to board!

Profile image
Meghan G.
Sitter Profile Image: Toni S.
Verified Background Check
Toni S.
Star Sitter
from
$25
per night
4.9 out of 5 stars
56 reviews
24 repeat clients
30 years of experience
DeForest, WI, 53532

Toni did a great job with our beagle while we were on vacation. She gave him a lot of personalized attention, took him on frequent visits to the dog park and other “field trips”, and sent us daily photo updates. We feel very comfortable leaving our dog in Toni’s care and would not hesitate to do so again in the future.

Profile image
Philip B.
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
27 reviews
7 repeat clients
15 years of experience
Stone Meadows, Madison, WI, 53719

We left our dog Toffee with Jenny and her family for 5 days while we attended a work conference, and we could not have asked for a better experience! This was our first time using Rover and leaving Toffee with someone we didn’t know, so we were definitely nervous at first. Jenny immediately made us feel comfortable with constant updates, pictures, and videos throughout the entire stay. Toffee had the absolute best time running around in her huge backyard, playing with her kids and her two dogs, and getting so much love and attention. It truly felt like he was treated as part of their family. You can tell Jenny genuinely cares about the dogs she watches. We were able to fully enjoy our trip knowing Toffee was happy, safe, and so well cared for. We are beyond grateful and will absolutely be booking with Jenny and her lovely family again in the future. Highly recommend!

Profile image
Manisha C.
Sitter Profile Image: Mary Z.
Verified Enhanced Background Check
Mary Z.
from
$50
per night
5.0 out of 5 stars
19 reviews
9 repeat clients
10 years of experience
Regent, Madison, WI, 53726

Remy had an amazing stay! He's a little special because of his tummy issues, so it is very hard for me to leave him at all, but it's just a little easier knowing he's in caring hands. Thank you so much for all of the photos and updates. I really appreciate all that you did to make him comfortable. Remy sends his love!

Profile image
Vianna A.
Sitter Profile Image: Evelyn R.
Verified Enhanced Background Check
Evelyn R.
from
$28
per night
1 repeat client
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: Lindsey C.
Verified Enhanced Background Check
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

Lindsay was quick to respond to all my messages and made it easy to arrange drop off and pick up. She sent a number of photos of my dog and took her for a number of long walks, just what the dog needs to balance her abundance energy. I would highly recommend her and will use her again.

Profile image
Holly K.
Sitter Profile Image: Allison C.
Verified Enhanced Background Check
Allison C.
Star Sitter
from
$40
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
5 years of experience
Glen Oak Hills, Madison, WI, 53705

Our three dogs had a great night with Allison! She was easy to work with and laid back. Dogs got to chill on the couch, luxury access to special beds and blankets. Thanks for a great stay!

Profile image
Ceri J.
Sitter Profile Image: Michelle S.
Verified Enhanced Background Check
Michelle S.
from
$50
per night
5.0 out of 5 stars
45 reviews
9 repeat clients
30 years of experience
Orchard Ridge Community, Madison, WI, 53711

Michelle was wonderful. She is super kind and so is her husband, Kevin. They handled my dog and his anxiety perfectly, couldn’t have asked for a better spot to board my dog :) he will definitely be my new go to when I need to go out of town!

Profile image
Mykenzie M.
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
46 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: Amy & Michael G.
Verified Enhanced Background Check
Amy & Michael G.
from
$35
per night
25 years of experience
Madison, WI, 53704

About: Hi! My name is Amy. My husband Michael and I grew up with dogs-both large and small. We acquired our first dog shortly after purchasing our home over 20 years ago. We have raised dogs in our home since they were puppies. We recently lost our cherished dog Maddie to cancer. We are not ready to own another dog at this time however we really miss having a furry friend in our home. We would love to care for your dog! We work from home and are available to take your dog out as needed to play in our large fenced in yard or out for a walk. We live in a dog friendly neighborhood and would love to care for your 4-legged family member. I currently work from home with a flexible schedule. I am able to give dogs consistent attention throughout the day. My husband works from home most afternoons and can be flexible with his schedule as well. We structure our days around feeding routines, potty breaks, walks, and downtime so dogs can settle in comfortably. We are mindful of maintaining your dog’s normal routine as closely as possible. We are happy to sit multiple dogs from the same client. We have a large, fenced in yard to run and play in. We can take your dog on leash for daily walks. We have a large crate that can be used upon request. We will provide updates to you during your dog's stay.

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

Easy pickup and drop off, friendly, updates with pictures of my dog during her 1 week stay with them. They got her to eat her breakfast every morning and play and she's a shy nervous girl!

Profile image
Rebecca D.
Sitter Profile Image: Yee Lam C.
Verified Enhanced Background Check
Yee Lam C.
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: David R.
Verified Enhanced Background Check
David R.
Star Sitter
from
$55
per night
5.0 out of 5 stars
182 reviews
86 repeat clients
15 years of experience
Columbus, WI, 53925

I had the pleasure of using David’s exceptional dog-sitting services. He cared for my yorkie-mix and labrador retriever for a short family vacation. His professionalism and welcoming nature made me feel comfortable leaving my pets in his care. His home, nestled amongst trees and with a secure yard, provided the perfect environment for my dogs. Regular updates and pictures he provided during my time away helped me relax. I would highly recommend David’s services to others.

Profile image
Nicole C.
Sitter Profile Image: Hannah P.
Verified Enhanced Background Check
Hannah P.
from
$60
per night
5.0 out of 5 stars
10 reviews
6 repeat clients
18 years of experience
Vilas, Madison, WI, 53711

Hannah and family were amazing! It was clear from the pictures she shared that they felt safe and happy while we were away. Hannah sent lots of pictures and was so easy to communicate with. We already have another reservation booked with her!!

Profile image
Amy P.
Sitter Profile Image: Ndaziona N.
Verified Enhanced Background Check
Ndaziona N.
from
$45
per night
5.0 out of 5 stars
5 reviews
1 repeat client
7 years of experience
Sun Prairie, WI, 53590

I would recommend Ndaziona to anyone who wants a great dog setter. Nikita was given best care anyone could ask for. During the time that she was with this family we continually got updates and pictures setting our mind at ease, knowing she was getting the best care we could have asked for. Again I would highly recommend this setter.

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

Cleda was amazing with our 8 year old little Datsun mix. she sent me pictures with updates about Lucy. She was very flexible with time pick up and drop off times. I am definitely going to use Cleda again as well as recommend her to others. Oh, I forgot to add she also gave me a little report card on how she did with eating, using the bathroom, getting along with others and so on when I picked her up. That was a great bonus.

Profile image
Saima C.
Sitter Profile Image: Da Yeon E.
Verified Background Check
Da Yeon E.
Star Sitter
from
$35
per night
5.0 out of 5 stars
91 reviews
25 repeat clients
7 years of experience
Vilas, Madison, WI, 53711

Da Yeon was amazing with our 3 month old kitten! I was so nervous leaving our kitten on a family trip since we had just adopted her. I was completely at ease that we picked Da Yeon to take care of her and would book with her in the future! Our kitten was very well cared for , we could tell she was so happy with her weekend visit! We also received photos which was fun to see how our kitten was doing. Would hands down recommend!

Profile image
Christine L.
Sitter Profile Image: Andrea P.
Verified Enhanced Background Check
Andrea P.
Star Sitter
from
$47
per night
5.0 out of 5 stars
18 reviews
5 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!

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

Robert was great with our puppy and provided regular updates. Very flexible with working with us on a pick up time when circumstances caused some big delays on our end.

Profile image
Andrew K.
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

Rebecca was great! She was very responsive and sent several pictures throughout Kylo's stay. I felt confident that Kylo was in good hands while we were away. I would definitely book with Rebecca again!

Profile image
Natalie N.
Boarding
5.0 out of 5 stars

Kris and her family took such amazing care of our pup! She was incredibly flexible with timing and even met up with us beforehand so she could get to know him. While we were away, she sent us tons of pictures, videos, and updates, which gave us so much peace of mind. We could tell he was happy and well cared for the whole time. We would 10000% recommend Kris and her family! ❤️

Profile image
Audrey D.
Boarding
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.

Profile image
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!

Profile image
Courtney N.
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

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 10
repeat pet boarding clients

FAQs for Boarding - Windsor

Frequently asked questions about Rover

The average cost for Pet Boarding in Windsor on Rover is $37.45 per night (as of September 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 449 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.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge