Dog Boarding Windsor

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Over 392
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: Sarah M.
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Sarah M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
124 reviews
17 repeat clients
35 years of experience
Deforest, WI, 53532

Our 2 dogs stayed at Sarah's for about a week earlier this month. The stay was great! We got daily updates, including photos and videos. They have a fantastic large fenced in yard where they could safety run and play. They had lots of playtime, but also lots of snuggles and love. They were both clearly enjoying their own vacation at Sarah's while we were gone on ours. It was so refreshing to know they were so well cared for while we were away- we have already rebooked them for our next trip!

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

Edith and her husband are absolutely amazing! They take such wonderful care of Henry, and every time we leave him with them, we have complete peace of mind knowing he’s in great hands. One thing we really appreciate is the thoughtful communication. The updates and photos are the perfect balance—frequent enough to reassure us that Henry is happy, comfortable, and well cared for, but never excessive. They always include just the right amount of detail, which makes it easy to relax and enjoy our time away. It’s obvious that they genuinely love dogs and treat Henry like part of their own family. We always come home to a happy, well-loved pup, and we couldn’t ask for a better experience. We highly recommend Edith to anyone looking for a trustworthy, caring, and dependable dog sitter!

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

Erik and his family were able to accommodate my last minute overnight dog sitting request. My dogs were so excited to greet their family. They were so kind and welcoming to me as well. They have a lovely fenced yard that my dogs just loved. I will absolutely be using them again.

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Catherine C.
Sitter Profile Image: Paula R.
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Paula R.
Star Sitter
from
$40
per night
5.0 out of 5 stars
89 reviews
27 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: Toni S.
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Toni S.
Star Sitter
from
$25
per night
4.9 out of 5 stars
55 reviews
24 repeat clients
30 years of experience
DeForest, WI, 53532

Toni was fantastic — Teo had an amazing time with her! She took him to the dog park three times during his 2-night stay, sent plenty of photos and updates, and clearly gave him lots of attention and care. I felt totally comfortable leaving Teo with her and will happily book her again. Highly recommend!

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Yuke H.
Sitter Profile Image: Ronalisa E.
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Ronalisa E.
from
$45
per night
5.0 out of 5 stars
37 reviews
15 repeat clients
6 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: Erika M.
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Erika M.
Star Sitter
from
$43
per night
4.9 out of 5 stars
147 reviews
79 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: Duane & Lauren S.
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Duane & Lauren S.
Star Sitter
from
$32
per night
5.0 out of 5 stars
91 reviews
28 repeat clients
30 years of experience
Ridgewood, Madison, WI, 53704

My boy stayed with Duane and Lauren and had a great time. They are so kind and communicative with pupdates throughout their stay. I have already recommended them to friends and will definitely use them again!

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Dory W.
Sitter Profile Image: Emily L.
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Emily L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
122 reviews
37 repeat clients
20 years of experience
Mc Farland, WI, 53558

Emily was great with our dogs kept us updated on how they were doing and sent lots of pictures. I think the dogs we sad that we came back for them, and that they didn't get to stay longer.

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Becky C.
Sitter Profile Image: Ben K.
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Ben K.
Star Sitter
from
$60
per night
5.0 out of 5 stars
126 reviews
27 repeat clients
15 years of experience
Eken Park, Madison, WI, 53704

Ben and Kassy are the best!!! DouDou is very shy but he already love them and make friends with lotus and buddha already! 😊 Will come back definitely!

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Peiqi Z.
Sitter Profile Image: Doua Song 'Jenny' & Darin K.
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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

Jenny and her family did an excellent job watching Teddy and giving him the best experience during the holidays. It was even his birthday and they went above and beyond to throw a birthday party for him! We are so appreciative of how well Teddy was treated and all the photo updates were reassuring. Teddy is looking forward to his next stay! Highly recommend! 🤍

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Maggie Y.
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

Jesse's great. He's terrific with Rosie and a great communicator. Worth every penny. He's my go-to when I have to go out of town and need dog care.

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Mark N.
Sitter Profile Image: Tony D.
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Tony D.
Star Sitter
from
$50
per night
5.0 out of 5 stars
190 reviews
65 repeat clients
25 years of experience
Madison, WI, 53718

Tony was good with communication and sent lots of pics of Merlin so I knew he was doing well. He’s been sleeping all day since he’s been home! Merlin loved his stay and playing with other dog friends there. Will definitely be booking with Tony again!

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Stephanie D.
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: Stephanie E.
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Stephanie E.
Star Sitter
from
$42
per night
5.0 out of 5 stars
26 reviews
8 repeat clients
18 years of experience
Madison, WI, 53704

Stephanie was great! She was easy to work with, took fantastic care of our pup. Our girl wasn't sure she wanted to leave. She sent lots of pictures and provided a fun and active environment. Would highly recommend!

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Holli H.
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
277 reviews
150 repeat clients
30 years of experience
Sun Prairie, WI, 53590

Val did great with our dogs, kept us informed and did everything we requested in terms of medications and feeding! Dogs came home wiped out and relaxed! Will definitely use in the future.

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Nicholas B.
Sitter Profile Image: Jenna H.
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Jenna H.
from
$31
per night
5.0 out of 5 stars
28 reviews
8 repeat clients
30 years of experience
Waunakee, WI, 53597

Jenna was wonderful taking care of our dog. She was attentive, friendly and happy to have our dog stay with her and her family. She sent us regular updates and photos during the stay. We would highly recommend Jenna and would book with her again.

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Arturo G.
Sitter Profile Image: Ellen S.
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Ellen S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
61 reviews
17 repeat clients
10 years of experience
Marshall, WI, 53559

Ellen was a great host for our sheepdog! Communication was excellent from start to finish. She sent pictures and video so we knew that Lucy was enjoying her time. Big fenced in backyard was a bonus. Highly recommend.

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Philip E.
Sitter Profile Image: Jessica M.
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Jessica M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
44 reviews
12 repeat clients
25 years of experience
Rolling Meadows, Madison, WI, 53714

The kids were happy. Good communication, lots of photos and video. It was a great place with a good yard for them to play. She took good care of our perrhijos.

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

Kris was absolutely fantastic. I felt very comfortable leaving Cokes with Kris and her household. Would not hesitate to use again. Thank you so much!

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Richard M.
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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

Our dogs had so much fun lots of pictures and they were tired when they arrived home. Super nice couple. Our dogs were so well taken care of definitely recommend. I hope they would watch our dogs again. I know they are a lot of energy.

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Christine S.
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

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.

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Julia L.
Boarding
5.0 out of 5 stars

Kris is great! Wagyu loves having a family and a home to go to and I love getting updates on what he's up to while knowing he's in great hands :)

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Madeleine S.
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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  • 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.

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Meet local sitters who will treat your dogs like family

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Popular requests for dog boarding - Windsor

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Sitters in Windsor average 11
repeat dog boarding clients

FAQs for Boarding - Windsor

Frequently asked questions about Rover

The average cost for Dog Boarding in Windsor on Rover is $36.63 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog 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 Dog Boarding. For more information on service fees, click here .

As of August 2026, there are 444 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 rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.

89% of Windsor sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Windsor landmarks or neighborhoods your dog is enjoying.

If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.

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.

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.

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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