Dog Boarding Lake Windsor

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Over 10
pet parents in Lake Windsor have booked dog boarding

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: Mattison & Eli H.
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Mattison & Eli H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 27 reviews
8 repeat clients
15 years of experience
Madison, WI, 53718

“Nakia’s stay with Eli and Mattison was a great success. She enjoyed their fenced in yard so much. Per her pictures, it looked like she settled right in. Once home, she settled right in again. That is a great thing. She tends to be somewhat nervous, but she was not at all. I believe Eli and Mattison are super caregivers for our Nakia. Thank you so very much. Hopefully, she will be able to stay there in the future.”

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Dottie R.
Sitter Profile Image: Sarah M.
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Sarah M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 129 reviews
18 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: Kaycee & Robert R.
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Kaycee & Robert R.
Star Sitter
from
$36
per night
5.0 out of 5 stars
• 40 reviews
6 repeat clients
16 years of experience
Heritage Heights, Madison, WI, 53714

“Last minute booking and sitter was super accommodating! Kept me posted with pics and videos. I felt super comfortable and that my pup was in good hands as soon as I walked in the door! Highly highly recommend!”

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Jessica V.
Sitter Profile Image: Jessica R.
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Jessica R.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 25 reviews
8 repeat clients
10 years of experience
Lake Edge, Madison, WI, 53716

“Jessica is great to work with and very kind and caring! She loved on our fur baby during vacation and was very communicative. She sent lots of pictures which we loved getting and daily updates. Would definitely recommend! She treated our pup like her own!”

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Kelli K.
Sitter Profile Image: Emily L.
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Emily L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 133 reviews
39 repeat clients
20 years of experience
Mc Farland, WI, 53558

“After my meet and greet with Emily, I was instantly at ease and knew my young golden retriever would be in good hands. She was very communicative, checking in with me every day to let me know how things were going and what they got up to, and she always included photos! Emily was very flexible both for drop-off/pickup and for stopping by her house over lunch for the first couple of days to check on my pup. Her having a golden retriever of her own and a couple of sweet kids who gave my dog so much love was also a bonus!”

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

“Val was such an amazing host! He treated our dog, Bella, like one of the family. I even got a super cute picture of Bella, and she looked so happy! We can't wait to book with Val again!”

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Karen P.
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: Mira D.
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Mira D.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 15 reviews
5 repeat clients
10 years of experience
Waunakee, WI, 53597

About: As a pet owner myself, I understand how important it is to trust the person caring for your fur babies. I currently have my sweet girl Nova at home and am comfortable with pets of different temperaments and needs. I strive to create a safe, stress free experience while keeping owners updated with lots of photos and messages. Whether your pet needs playtime, cuddles, medication, or just a consistent routine, I’ll make sure they receive attentive care. I’m currently a SAHM with a very flexible schedule, allowing me to provide reliable care and accommodate a variety of pet care needs throughout the day. Your pets are treated like family! I have 1 cat in my home currently that is okay with dogs that visit. I maintain a clean, safe, and pet-friendly environment and carefully supervise interactions at all times.

Sitter Profile Image: Ruth B.
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Ruth B.
from
$50
per night
5.0 out of 5 stars
• 4 reviews
30 years of experience
Madison, WI, 53704

“⭐⭐⭐⭐⭐ Wonderful, trustworthy, and genuinely caring dog sitter! I cannot recommend Ruth highly enough! She took wonderful care of my dog, Titou, and I couldn’t have asked for a better experience. Ruth was responsible, attentive, trustworthy, and genuinely committed to making sure Titou felt comfortable, happy, and safe. I particularly appreciated her excellent communication and regular updates, which gave me tremendous peace of mind while we were apart. Ruth clearly understands that every dog has their own personality, needs, and routines. She approaches pet care with patience, kindness, and genuine affection. She provided a welcoming, secure environment where Titou felt completely at home. Finding someone you can truly trust with your beloved companion is invaluable. Titou was happy, relaxed, and clearly well cared for. I would absolutely trust Ruth with him again and wholeheartedly recommend her to anyone looking for a reliable, compassionate, and conscientious dog sitter!”

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Britt Marie Z.
Sitter Profile Image: Margaret L.
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Margaret L.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 36 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: Jennifer J.
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Jennifer J.
Star Sitter
from
$37
per night
4.9 out of 5 stars
• 11 reviews
5 repeat clients
6 years of experience
Lake Edge, Madison, WI, 53716

“Jennifer was communicative and responsive - updates and video of my dog and her dog playing like longtime pals. My dog was calm and relaxed when I picked her up, which has not always been the case with Dogsitter’s. Thank you Jennifer!”

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Diane F.
Sitter Profile Image: Amanda K.
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Amanda K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 197 reviews
65 repeat clients
20 years of experience
Cottage Grove, WI, 53527

“Amanda and her family were extremely accommodating and took care of my dog like he was their own. It was my first time using the app and I was nervous but she put that at ease with updates and pictures. Would definitely book again!”

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John S.
Sitter Profile Image: Tanya & Hutch K.
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Tanya & Hutch K.
from
$45
per night
5.0 out of 5 stars
• 6 reviews
30 years of experience
Monona, WI, 53716

“My dog’s week with Tanya & her dog, Zuki, couldn’t have been better! Tanya was attentive to my dog’s needs, he enjoyed running around her fenced yard & played enthusiastically with the resident dog, Zuki. Tanya sent frequent photos & video updates. She went above & beyond with Miles, noticing his need for mental stimulation & giving him puzzles & time to practice new tricks. I wouldn’t hesitate to book a sit at Tanya & Hutch’s place again—their wonderful care made being away from my dog much easier!”

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Kristina N.
Sitter Profile Image: Maria & Bryan P.
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Maria & Bryan P.
from
$35
per night
5.0 out of 5 stars
• 8 reviews
3 repeat clients
30 years of experience
Waunakee, WI, 53597

“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.
Sitter Profile Image: Ndaziona N.
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Ndaziona N.
from
$50
per night
5.0 out of 5 stars
• 8 reviews
2 repeat clients
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.”

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John A.
Sitter Profile Image: Laura D.
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Laura D.
from
$35
per night
5.0 out of 5 stars
• 60 reviews
18 repeat clients
35 years of experience
Mount Horeb, WI, 53572

“Laura welcomed our Barley into her home with open arms. She allowed us to come with Barley and check things out before having Barley stay with her. Shadow, Laura's massive golden retriever, is the friendliest pup around and gave Barley the opportunity to learn all the tricks around the house! :) We are so very lucky to have found Laura (and Shadow) and plan to have this be Barley's home away from home in the future!”

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Tom M.
Sitter Profile Image: Sarah P.
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Sarah P.
from
$50
per night
5.0 out of 5 stars
• 4 reviews
20 years of experience
Marshall, WI, 53559

“Sarah was wonderful with Jake and Meme while we were away for a couple of days! She had great communication, kept us updated, and did a fantastic job picking up on their individual cues and personalities. It gave us peace of mind knowing they were in good hands. Thanks so much for taking such great care of them, Sarah! We really appreciate everything!”

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Michele S.
Sitter Profile Image: Ricardo S.
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Ricardo S.
from
$40
per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
14 years of experience
Regent, Madison, WI, 53705

“Ricardo (and Maggie) were awesome with Leo. He clearly was engaged until he could just do no more. Ricardo hosted him during a football game for us, and Leo slept the 4.5 hour drive home and then through out the night and long into the next morning! I definitely hope to be able to have him host Leo for us again when we are back in Madison.”

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Kelly E.
Sitter Profile Image: Kris A.
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Kris A.
from
$40
per night
5.0 out of 5 stars
• 14 reviews
4 repeat clients
16 years of experience
DeForest, WI, 53532

“Great experience working with Kris again for Clementine! Kris was even kind enough to drop off Clementine at home for us since our flight was getting in late and we live a little ways away. Will definitely use her again as a sitter!”

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Ashley M.
Sitter Profile Image: Marlene S.
Verified Enhanced Background Check
Marlene S.
from
$50
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
15 years of experience
Eastmorland, Madison, WI, 53714

“From the beginning, Marlene was extremely flexible in coordinating Freya’s stay. Throughout Freya’s stay, I received consistent updates and pictures, which made me smile each time I saw them. I could tell, both from the pictures and from Freya’s great mood when I arrived for pick up, that she had fun and felt comfortable with Marlene. I was thrilled with Marlene’s services, and I would trust Freya with her any time. I highly recommend Marlene to anyone!!”

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Pete T.
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The median cost per night for dog boarding in Lake Windsor is $45

Dog parents share their Rover experiences - Lake Windsor

1 / 1
5.0 out of 5 stars

Maria and Bryan were great taking care of our beagle and making him feel welcomed. We appreciated the photo updates.

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Philip B.
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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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.

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

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

Popular requests for dog boarding - Lake Windsor

Select a filter and find qualifying sitters offering dog boarding.

Sitters in Lake Windsor average 11
repeat dog boarding clients

FAQs for Dog Boarding - Lake Windsor

Frequently asked questions about Rover

The average cost of Dog Boarding in Lake Windsor is $39 per night as of November 2026. Most bookings cost between $39 and $45 per night. On Rover, 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 November 2026, there are 442 sitters on Rover offering Dog Boarding across Lake Windsor. Enter your ZIP code to see which available sitters are closest to your home.

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.

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.

93% of sitters in Lake 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 Lake 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 Lake Windsor.

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

Yes, you can find sitters who have experience with handling special pet needs in Lake Windsor. On Rover:

  • 89% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 93% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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 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.

Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.

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