Dog Boarding Windsor

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Over 398
pet parents in Windsor have booked dog boarding

Windsor, Find top rated dog 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: Paula R.
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Paula R.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 93 reviews
28 repeat clients
5 years of experience
Southeast, DeForest, WI, 53532

“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.
Sitter Profile Image: Erik R.
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Erik R.
from
$30
per night
4.9 out of 5 stars
• 38 reviews
13 repeat clients
15 years of experience
Sun Prairie, WI, 53590

“They were absolutely amazing with Heidi! She’s a senior pup, and even after she had a lot accidents in their home (I was so embarrassed 🤦🏽‍♀️), they didn’t hesitate to work with her. Instead of refusing to care for her, they came up with a great solution, and everything went smoothly for the rest of her stay. They even said they’d be happy to have her back! They are such a kind, understanding family, and I would highly recommend them to anyone looking for someone to care for their pets.”

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Rachel v.
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
• 280 reviews
151 repeat clients
30 years of experience
Sun Prairie, WI, 53590

“Val took amazing care of our dogs and also was extra attentive in walking us through the entire Rover experience since this was our first time. We picked up very happy and healthy dogs today and couldn’t have been more thrilled by the experience. Thank you so much, Val! Because of you and your updates/pictures we were able to take a much needed vacation without worrying about our fur babies.”

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Christine D.
Sitter Profile Image: Edith S.
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Edith S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 86 reviews
27 repeat clients
20 years of experience
Waunakee, WI, 53597

“We absolutely, 100% recommend Edith S. as a pet sitter. She is thoughtful, kind and really loved our little dog while we were gone. Multiple pictures and little stories daily put us completely at ease while we gone. We feel very lucky and grateful to have found her.”

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Clint B.
Sitter Profile Image: Duane & Lauren S.
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Duane & Lauren S.
Star Sitter
from
$32
per night
5.0 out of 5 stars
• 93 reviews
29 repeat clients
30 years of experience
Ridgewood, Madison, WI, 53704

“Duane and Lauren were wonderful to work with and took great care of our two dogs!!! Their communication was terrific and they were very flexible. We would love to have our dogs stay with them again!!”

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Dave W.
Sitter Profile Image: Erika M.
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Erika M.
Star Sitter
from
$43
per night
4.9 out of 5 stars
• 147 reviews
80 repeat clients
13 years of experience
Sun Prairie, WI, 53590

“This was the first time we used Rover/had someone else watch our 1.5 year old Irish Doodle and it went great! Erika was incredibly responsive and so patient and kind with us since we had a lot of questions and back and forth with it being a new experience! She was flexible, a wonderful companion and gave us some great feedback regarding Evie! We would absolutely have Evie stay here again if we needed someone!”

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Brittany B.
Sitter Profile Image: Ronalisa E.
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Ronalisa E.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 39 reviews
15 repeat clients
7 years of experience
Madison, WI, 53704

“Rona took excellent care of our high energy dog! He absolutely loved getting to explore and sniff around her spacious backyard, and he was very exhausted when we picked him up. We appreciated her daily updates and pics/videos. This was our first time having Rona take care of our dog, and we would happily book with her again.”

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Julie D.
Sitter Profile Image: Amanda K.
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Amanda K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 195 reviews
64 repeat clients
20 years of experience
Cottage Grove, WI, 53527

“Amanda and Paul’s family is wonderful. I can’t say enough good things. They are loving and sweet, and experienced will all types of dogs. I felt really safe and happy to be leaving my pup in their care.”

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Pamela T.
Sitter Profile Image: Sarah M.
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Sarah M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 126 reviews
17 repeat clients
35 years of experience
Deforest, WI, 53532

“Lunar was so very well taken care of while we were on a trip. Sarah sent updates and helped us figure out care when our flight was delayed. It gives us such peace of mind every time Sarah cares for our active dog!”

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Jessica C.
Sitter Profile Image: Mattison & Eli H.
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Mattison & Eli H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 18 reviews
5 repeat clients
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.”

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Cole O.
Sitter Profile Image: Stephanie E.
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Stephanie E.
Star Sitter
from
$42
per night
5.0 out of 5 stars
• 29 reviews
11 repeat clients
18 years of experience
Madison, WI, 53704

“Absolutely fantastic! Gave Odin so love, attention, and exercise! Gave updates throughout the week. Could not have asked for anyone better to care for my dog while I was away!”

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Whitney P.
Sitter Profile Image: Chelssey H.
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Chelssey H.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 27 reviews
12 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: Kaycee & Robert R.
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Kaycee & Robert R.
Star Sitter
from
$36
per night
5.0 out of 5 stars
• 38 reviews
6 repeat clients
16 years of experience
Heritage Heights, Madison, WI, 53714

“Our dog stayed with Kaycee and her family for 10 days, and we had a wonderful experience. She sent me photos every day, and they took him for walks even though they have a fenced backyard. The kids in the family gave Swift lots of attention, and he played with their family dog. Very sweet family — I highly recommend them for dog boarding.”

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Anna M.
Sitter Profile Image: Stefanie B.
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Stefanie B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 98 reviews
31 repeat clients
14 years of experience
Middleton, WI, 53562

“Stephanie was an amazing sitter. She messaged me daily with pictures too. Walks, playtime and belly rubs were a daily occurrence with Mack. I was afraid he wouldn’t want to come back home. 😊”

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Shelly K.
Sitter Profile Image: Jessica M.
Verified Enhanced Background Check
Jessica M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 47 reviews
13 repeat clients
25 years of experience
Rolling Meadows, Madison, WI, 53714

“Jessica was absolutely wonderful!! She took amazing care of my dog Maisie. My dog had so much fun with her and the other dogs. Jessica helped manage her allergies and was in contact with me everyday with updates, pictures, and videos. Would definitely book with her again. You can tell she cares a lot n treated my dog as her own she was in such good hands. I could enjoy my vacation without worrying. She’s so wonderful!!! Cant thank her enough for taking care of my baby girl.”

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Jennifer D.
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
• 109 reviews
31 repeat clients
2 years of experience
Madison, WI, 53719

“Kristin and Bruce did a great job with my older dog, Madigan. She is sometimes anere xious to be away from home, but she was at ease from the minute we walked in the door. This is the first time in the last six years we did not have someone come in to the home. The pictures showed a relaxed, happy dog and her tail and ears were high when I arrived to pick her up. Dogs know people and she is loyal to "her pack", but our dog loved being a part of Kristin and Bruce's pack. I highly recommend Kristin and Bruce. You will not be disappointed!”

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Brian D.
Sitter Profile Image: Brandon & Katy S.
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Brandon & Katy S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 10 reviews
3 repeat clients
15 years of experience
Worthington Park, Madison, WI, 53714

“Brandon and Katy are lovely! They were very helpful moving my dog's crate and getting him settled. Sammy had a great time playing and cuddling.”

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Kara B.
Sitter Profile Image: Margaret L.
Verified Enhanced Background Check
Margaret L.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 33 reviews
8 repeat clients
10 years of experience
Emerson East, Madison, WI, 53704

“Drop off and pick were super smooth. Benji had zero complaints about his over-night with Margaret ;) We will definitely book with Margaret again!”

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Jessica V.
Sitter Profile Image: Lindsey C.
Verified Enhanced Background Check
Lindsey C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 43 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: Katie & Samuel W.
Verified Enhanced Background Check
Katie & Samuel W.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 32 reviews
13 repeat clients
20 years of experience
MIDDLETON, WI, 53562

“Katie and Samuel were great to Jarvis and sent us several updates throughout his stay. They also have a gated backyard to help with energetic dogs. I would highly reccomend!”

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Justin L.
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The median cost per night for dog boarding in Windsor is $45

Dog parents share their Rover experiences - Windsor

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5.0 out of 5 stars

I highly recommend Paula, especially for special needs dogs! I can tell my little guy was very loved and had a great time during his stay. Thank you!

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Elyse M.
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 dogs like family

  1. 1. Search

    Browse profiles of sitters near you who offer dog 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 dog boarding - Windsor

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Sitters in Windsor average 10
repeat dog boarding clients

FAQs for Dog Boarding - Windsor

Frequently asked questions about Rover

The average cost of Dog Boarding in Windsor on Rover is $37 per night as of October 2026. Most bookings cost between $27 and $61 per night. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 448 sitters on Rover offering Dog Boarding across Windsor. Enter your ZIP code to see which available sitters are closest to your home.

Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.

88% of sitters in Windsor can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.

During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Windsor home-away-from-home, we recommend packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Windsor.

<b>Tip:</b> You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

You and your Windsor sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

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.

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.

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

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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