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 404
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: Tony D.
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Tony D.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 199 reviews
69 repeat clients
25 years of experience
Madison, WI, 53718

“We have used Tony multiple times for our dog Mishu now. She absolutely loves coming over and playing with other dogs. Tony gives us great peace of mind while on vacation knowing how loved our dog is there! Thanks Tony! 😁”

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Valarie H.
Sitter Profile Image: Amy & Michael G.
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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: Kristin & Bruce M.
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Kristin & Bruce M.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 107 reviews
31 repeat clients
2 years of experience
Madison, WI, 53719

“Kristin, Bruce, and their family took great care of Tony for our weekend away. We received regular updates with photos of Tony while we were away. We would definitely book a stay again. Thank you so much!”

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Hannah & Eli W.
Sitter Profile Image: Stefanie B.
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Stefanie B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 92 reviews
29 repeat clients
14 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: Ben K.
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Ben K.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 132 reviews
29 repeat clients
15 years of experience
Eken Park, Madison, WI, 53704

“Nala’s usually quite shy especially with initial meetings but she was immediately fairly comfortable and seemed so relaxed when we came to pick her up. Ben is very thorough with verifying care information and he gives frequent updates. Great communication and great care. We will definitely be requesting their services again!”

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Ashley W.
Sitter Profile Image: Jackie G.
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Jackie G.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 68 reviews
18 repeat clients
20 years of experience
SUN PRAIRIE, WI, 53590

“Jackie and her family were great! Our dog got along with her dog and he came back tired from so much play. He definitely would go back! Thanks!”

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Angie N.
Sitter Profile Image: Evelyn R.
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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: Holly & Ana Maria P.
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Holly & Ana Maria P.
from
$22
per night
12 years of experience
Schenk-Atwood-Starkweather-Yahar, Madison, WI, 53704

About: Have three dogs and four cats and have fostered more than 100 animals. Whether babies or seniors, we have the patience and experience to care for your animals while you are away! We work from home, so available to care for your pets in your home or in ours. In our home, cat sitting is preferred. If needing assistance in your home, we would be glad to assist you with your dogs and cats! In our home, we have a fenced in backyard and allow the animals free range of the home. Pets are on scheduled feeding times, and the dogs also receive regular walks. If you have specific dietary concerns with your animals or scheduled activities, we will ensure those needs are met.

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
8 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!”

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Mary R.
Sitter Profile Image: Jessica M.
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Jessica M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 46 reviews
13 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: Chelssey H.
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Chelssey H.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 20 reviews
11 repeat clients
16 years of experience
Madison, WI, 53711

“Chelssey was awesome! Great communication prior and during Sunny’s stay which I loved! She also sent pictures which was fun. We will book again with Chelssey.”

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Carol D.
Sitter Profile Image: Shawn S.
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Shawn S.
from
$45
per night
5.0 out of 5 stars
• 10 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: Allison C.
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Allison C.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 11 reviews
3 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!”

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Ceri J.
Sitter Profile Image: Jennifer J.
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Jennifer J.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 8 reviews
5 repeat clients
6 years of experience
Lake Edge, Madison, WI, 53716

“Lucy had a great weekend with Jennifer! She got along great with Oscar. Tick season is pretty bad this year and Jennifer made sure to look over Lucy and keep her tick-free!”

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Chuck S.
Sitter Profile Image: Emily L.
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Emily L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 37 reviews
14 repeat clients
25 years of experience
Sun Prairie, WI, 53590

About: I’ve been an animal lover and care taker as long as I can remember. I grew up in the country and was always finding stray animals that needed nursed back to health. I have a very flexible schedule right now. Can do any time of day, any day of the week. I am extremely active and love playing and walking with animals. I will follow instructions to a tee no matter how specific. There will never be judgment. I will remain extremely cautious and present in my interactions.

Sitter Profile Image: Brad N.
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Brad N.
Star Sitter
from
$42
per night
5.0 out of 5 stars
• 105 reviews
22 repeat clients
35 years of experience
Fitchburg, WI, 53711

“Brad was a good boarder for our dog, Bear. He provided a few messages about how Bear was settling in and getting on throughout his stay. Bear had nothing but good things to say about his stay with Brad. 5/5 would recommend. Just don't book him on the dates I'll need him!”

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Rob K.
Sitter Profile Image: Payton W.
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Payton W.
from
$30
per night
5.0 out of 5 stars
• 36 reviews
14 repeat clients
7 years of experience
Capitol, Madison, WI, 53703

“Payton was very communicative with us in regards to our little doggy. She sent videos and text regularly and we felt reassured knowing that our pet was in great hands with Payton we will use her again and highly recommend!”

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Renee K.
Sitter Profile Image: Tonisha A.
Verified Background Check
Tonisha A.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 57 reviews
16 repeat clients
30 years of experience
Sun Prairie, WI, 53590

“Tonisha treated my dog Sophie with care. Sophie is a very anxious pup, so I was nervous about leaving her. Tonisha took pictures and gave me updates throughout the three days stay. Sophie did just fine and I would recommend Tonisha to take care of your fur baby.”

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Deb M.
Sitter Profile Image: Jesse L.
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Jesse L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 19 reviews
8 repeat clients
12 years of experience
Emerson East, Madison, WI, 53704

“Thank you Jesse! You made this a lot easier than we thought it'd be. This was our first time boarding Tank and we're glad we chose you. Thanks again for caring for him while we were away. The pictures and video were a bonus. Thank you!”

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Jacky T.
Sitter Profile Image: Kara S.
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Kara S.
from
$40
per night
4.7 out of 5 stars
• 92 reviews
29 repeat clients
10 years of experience
Reston Heights, Madison, WI, 53718

“Best in home dog care around! Kara takes exceptional care of our dog and our dog loves spending time with her and her animals. We appreciate the care and peace of mind knowing our dog is in good hands provides.”

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Terah S.
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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

Paula was awesome with our little guy! We appreciated the pictures and updates she sent. We could tell our dog felt right at home with her.

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Suzanne S.
Boarding
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!

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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! ❤️

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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.

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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

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
  3. 3. Book & Pay

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

Popular requests for pet boarding - Windsor

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Sitters in Windsor average 10
repeat pet boarding clients

FAQs for Pet 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.

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