Dog Boarding Lake Windsor

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Lake 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: 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

“This was Gatsby’s second time staying with Edith and he had a blast. The second we pulled up to Edith’s house he lost his mind with excitement realizing where we were! Edith sent frequent updates and photos and I knew Gatsby was getting the best care. Thanks Edith!”

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Shay C.
Sitter Profile Image: Paula R.
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Paula R.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 94 reviews
29 repeat clients
5 years of experience
Southeast, DeForest, WI, 53532

“She treated My dog like it was her own. He loved being there and was well cared for. Highly recommend Paula, she will be my go to anytime I need Benny to be cared for.”

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Dilenia C.
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
• 96 reviews
32 repeat clients
30 years of experience
Ridgewood, Madison, WI, 53704

“Such a treat to have Duane & Lauren take care of my pup, Rapha while I was away. They are very responsive and attentive to the needs of both owner and doggie. Thank you!”

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Russhell C.
Sitter Profile Image: Stefanie B.
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Stefanie B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 108 reviews
40 repeat clients
14 years of experience
Middleton, WI, 53562

“Stefanie was just the sweetest sitter for our Delphi. She did a great job communicating with us while we were away, sending us cute photos, and assuring us that our sweet pup was being taken care of. I will definitely ask for Stefanie next time I need a sitter!”

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Kristina D.
Sitter Profile Image: Jennifer J.
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Jennifer J.
Star Sitter
from
$37
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: 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 Baylee's first boarding experience since I adopted her and she seems very happy and healthy. She loves walks and Erika provided multiple daily walks. Baylee's medication and feed requirements were met. I couldn't expect more than a happy dog!”

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Patti P.
Sitter Profile Image: Amy & Michael G.
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Amy & Michael G.
from
$40
per night
5.0 out of 5 stars
• 2 reviews
25 years of experience
Madison, WI, 53704

“Amy and Michael took great care of Trini! They provided daily updates and pictures. We will definitely be taking her again to stay with them. Thanks so much!”

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Cristina M.
Sitter Profile Image: Katie & Samuel W.
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Katie & Samuel W.
from
$45
per night
5.0 out of 5 stars
• 33 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.
Sitter Profile Image: Margaret L.
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Margaret L.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 34 reviews
8 repeat clients
10 years of experience
Emerson East, Madison, WI, 53704

“Margaret took excellent care of our new rescue for a 2 day boarding. She was super easy to communicate with and responded quickly, sent regular updates, pictures, and videos, and clearly goes the extra mile to make sure your dog is well cared for. We will 100% be booking with her in the future for any dog sitting needs!”

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Alma & Samuel F.
Sitter Profile Image: Andrea P.
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Andrea P.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 21 reviews
6 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.”

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Matt S.
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

“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!”

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Rebecca D.
Sitter Profile Image: Ryan & Martha M.
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Ryan & Martha M.
Star Sitter
from
$41
per night
5.0 out of 5 stars
• 60 reviews
26 repeat clients
14 years of experience
Stone Meadows, Madison, WI, 53719

“Ryan and Martha and their family have been a saving grace for me! Willow loves going over there, and clearly feels right at home. They send photos throughout her stay, and are so gracious with their time and thoughtfulness.”

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Ashley D.
Sitter Profile Image: Hannah P.
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Hannah P.
from
$60
per night
5.0 out of 5 stars
• 12 reviews
7 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!!”

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Amy P.
Sitter Profile Image: Yee Lam C.
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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!”

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Mohini G.
Sitter Profile Image: Sarah H.
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Sarah H.
from
$40
per night
5.0 out of 5 stars
• 42 reviews
17 repeat clients
10 years of experience
Verona, WI, 53593

“Sarah was wonderful! She was very communicative and it was clear that Sunny was being well loved while we were away. Lots of walks and attention throughout the week. We feel very lucky that Sunny received great care when we were gone ❤️”

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Alisa S.
Sitter Profile Image: Renita L.
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Renita L.
from
$40
per night
5.0 out of 5 stars
• 6 reviews
15 years of experience
Waunona, Madison, WI, 53713

About: Animals have been an integral part of my life for as long as I can remember—from growing up around my family’s German Shepherd breeding and training work, to years of rescuing and fostering both dogs and cats. I can provide continuous supervision, regular potty and play breaks, and plenty of outdoor exercise tailored to each dog's energy level and temperament. My home currently includes one calm, dog-friendly resident cat, making for a peaceful, low-stress environment where guest dogs receive focused care and affection. I have worked with senior dogs and cats as well as puppies and kittens. I am experienced with administering medications and experienced with disabled dogs. I work remotely and am home full-time with a flexible work schedule. I can provide 24/7 care for your dog or cat. I am also available for walks throughout the day and week. While boarding in my home, I am able to be available for feeding or potty breaks as needed. I am able to watch the dog or cat to see what they need when. If I am providing drop in visits or walks, my schedule is flexible. I am available during the day and evenings.

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

“Cleda was awesome! She took care of our dog as well as we would have ourselves. Frequent updates, communication, and feedback; and a really great environment are just some of the great points.”

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Ares A.
Sitter Profile Image: David R.
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David R.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 186 reviews
87 repeat clients
15 years of experience
Columbus, WI, 53925

“David is one of the very few people we have grown to trust with our baby Jynx. She loved going to his house to play and always cones back tired and happy! Another great visit!”

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Trish R.
Sitter Profile Image: Manu J.
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Manu J.
from
$69
per night
5.0 out of 5 stars
• 66 reviews
11 repeat clients
30 years of experience
Madison, WI, 53715

“Izzy had a great stay with Manu again! We received pictures daily, of her spending time outside and relaxing on the couch. Manu also made sure she stayed cool in the extreme heat over the weekend. We'd happily board Izzy with Manu again in the future!”

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

“Brad communicates clearly and in an extremely timely fashion. His price is affordable. Easy drop off and pick up in a beautiful area. My dog came out extremely happy after her stay with Brad!! I will definitely be booking again in the future.”

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Addy G.
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Dog parents share their Rover experiences - Lake Windsor

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5.0 out of 5 stars

Marysia and Bryan did a great job taking care of Lyla. Sent lots of updates and their dogs were super fun for her to play with!

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Sara S.
Boarding
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
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  • 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.

How to book dog boarding

  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

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FAQs for Dog Boarding - Lake Windsor

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

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.

Depending on the sitter, their home environment, and your dog’s needs, daily exercise 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 Lake Windsor home-away-from-home, 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 Lake 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 Lake 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 , 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 .

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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