Dog Boarding in Wind Lake, WI

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Top rated Wind Lake dog boarders

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: Sandy D.
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Sandy D.
Star Sitter
from
$30
per night
5.0 out of 5 stars
193 reviews
74 repeat clients
40 years of experience
Mount pleasant, WI, 53406

Oh my goodness! I feel like we hit the jackpot with Sandy. She loves our little JoJo as if she were her own. JoJo runs to Sandy and is so happy when she is with her. It gives us great comfort to be out for the day, evening, or overnight, knowing JoJo is not in a crate and is spoiled. I love that Sandy plays with her, cuddles with her, and loves her. Sandy is the very best. My only hesitation in sharing this review is that others put her in such demand that we won't have access to her! But we love Sandy, so we will share this gem!

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Yvonne Z.
Sitter Profile Image: Maria & Nayibe B.
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Maria & Nayibe B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
380 reviews
117 repeat clients
20 years of experience
Brookfield, WI, 53005

This was our first time using Rover and our first time having someone that wasn’t family watch our dog. Wallen had so much fun and came home so happy ! We got frequent pictures, videos and updates so we knew he was very well taken care of!

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Taylor N.
Sitter Profile Image: Christina W.
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Christina W.
from
$40
per night
5.0 out of 5 stars
19 reviews
12 repeat clients
15 years of experience
Muskego, WI, 53150

Thanks for taking care of Raider while we were out of town. I am glad that he was able to find a friend to teach him the ropes. The daily pictures were a blessing which we hope will continue in the future.

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Chuck R.
Sitter Profile Image: Laura N.
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Laura N.
Star Sitter
from
$41
per night
5.0 out of 5 stars
21 reviews
5 repeat clients
20 years of experience
Southpoint, Milwaukee, WI, 53221

Laura did amazing with Romeo, she updated us everyday on how he was doing and was very responsive. Romeo was in very good hands. We would definitely use her again!

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Kyle A.
Sitter Profile Image: Kam O.
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Kam O.
Star Sitter
from
$55
per night
5.0 out of 5 stars
42 reviews
20 repeat clients
20 years of experience
Waterford, WI, 53185

Kam was an answer to my prayers! There are just sometimes I have to be away where my dog, a toy Aussie, can’t go, but I always hated taking him to a kennel. Somehow I found Rover and that led me to Kam. After a meet and greet I knew this was good. Kam, her family and her pets welcomed Cosmo in and treated him like family. She sent pictures several times a day. This was perfect for me to be able to leave him without feeling bad. He had lots of fun there. So glad I found Rover and Kam! It feels good!

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Becky M.
Sitter Profile Image: Debbie L.
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Debbie L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
72 reviews
18 repeat clients
50 years of experience
Oak Creek, WI, 53154

Debbie was great! She was very on top of things with my pup Reggie. She set up a meet and greet ahead of time to ensure we were both comfortable with Reggie spending the night and it put my mind at ease. I completely trust her to take great care of my pup. Highly recommend!

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Allie D.
Sitter Profile Image: Carol &  Steve B.
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Carol & Steve B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
15 reviews
5 repeat clients
25 years of experience
Muskego, WI, 53150

Carol and Steve are absolutely wonderful. They care deeply for pets and have the perfect set-up for doggies in their home. My husband and I have struggled to figure out who might offer a service such as this. And, there they were on Rover.com! Their home is very welcoming and the fenced yard is a wonderful space for dogs to explore. After a stay, our doggies Fiona and Wesley come home happy, content and with a smile!

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Esther K.
Sitter Profile Image: Joanne V.
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Joanne V.
Star Sitter
from
$50
per night
5.0 out of 5 stars
17 reviews
4 repeat clients
5 years of experience
Waukesha, WI, 53189

Gracie had an amazing stay with Joanne (& her family!) I enjoyed the communications and pictures during Gracie’s time in their home. Gracie enjoyed playtime with the kids and with the resident dog, Olivia. She had her kennel available, but enjoyed cuddles with their teenage son and quickly made herself a part of the family. I will certainly consider booking for future stays, and recommend Joanne to others!

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Kim S.
Sitter Profile Image: Kellene M.
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Kellene M.
Star Sitter
from
$36
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
40 years of experience
St. Francis, WI, 53235

We had a great experience with Kellene taking care of our pup. She was very responsive before and during the stay, and sent many updates/photos. Ozzy and coco got along great and it was nice to have a meet and great before to make sure the stay would go well. She treated Ozzy like her own pup and took him for walks, lots of play time and cuddles. We couldn’t ask for anything more!

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isis s.
Sitter Profile Image: Katy & Dennis "DJ" G.
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Katy & Dennis "DJ" G.
Star Sitter
from
$38
per night
5.0 out of 5 stars
112 reviews
39 repeat clients
35 years of experience
Wales, WI, 53183

Katy and DJ are wonderful sitters! We are so at peace leaving our dog Milo in their care. They send us frequent updates and pictures. Milo is worn out by the time he comes home. He loves his walks and playing with their pup! I would highly recommend them!

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Deb P.
Sitter Profile Image: Scott S.
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Scott S.
from
$35
per night
5.0 out of 5 stars
17 reviews
4 repeat clients
15 years of experience
Honey Creek Parkway, Milwaukee, WI, 53214

Scott and his dog Lucy were a great match for Roo! I received multiple picture updates and he was great at communicating. We met up beforehand to ensure a good match, and it was clear Scott has a natural way with dogs. Would gladly rebook!

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Jack P.
Sitter Profile Image: Savannah S.
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Savannah S.
Star Sitter
from
$38
per night
5.0 out of 5 stars
19 reviews
8 repeat clients
8 years of experience
New Berlin, WI, 53151

Savanah did a great job watching my dog over a weekend. Her dogs were extremely friendly with mine and my dog had a wonderful time. Would definitely recommend booking with Savanah.

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Alex G.
Sitter Profile Image: Lisa W.
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Lisa W.
Star Sitter
from
$38
per night
5.0 out of 5 stars
348 reviews
100 repeat clients
30 years of experience
Bay View, MILWAUKEE, WI, 53207

Lisa was so great with my nervous dog. You can tell, and my dog could tell, that’s she’s a pet lover. My dog latched on to her and Lisa was very reassuring sending pictures and updates letting me know my dog was in good hands. I was able to relax more on my vacation knowing ZeZe was being well cared for!

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Kristen K.
Sitter Profile Image: Ashley R.
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Ashley R.
Star Sitter
from
$45
per night
5.0 out of 5 stars
37 reviews
18 repeat clients
20 years of experience
Mount Pleasant, WI, 53406

Ashley and her family took excellent care of my Little Lucy! She sent us pictures of Lucy sunbathing and taking walks with the family. Definitely will have them watch her again!

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Lori S.
Sitter Profile Image: Scott & Ashley S.
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Scott & Ashley S.
Star Sitter
from
$44
per night
5.0 out of 5 stars
88 reviews
22 repeat clients
20 years of experience
Waukesha, WI, 53186

This was my first time using Rover. I couldn’t have picked a better family to look after my 2 girls while I was out of town. Scott sent picks and videos every day while yo was gone showing how much fun they were having.

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Michael S.
Sitter Profile Image: Kathy & Brad K.
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Kathy & Brad K.
Star Sitter
from
$40
per night
5.0 out of 5 stars
61 reviews
23 repeat clients
30 years of experience
Greendale, WI, 53129

Benny has been at Kathy's before for daycare. This was his first overnight stay. Kathy is so good about keeping me updated with pictures and treats Benny like he is one of her own. After some not so good experiences at other facilities I'm thrilled that Benny feels so comfortable at Kathy's and loves to play with her little doggo.

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Carol H.
Sitter Profile Image: Dana H.
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Dana H.
Star Sitter
from
$45
per night
5.0 out of 5 stars
18 reviews
10 repeat clients
8 years of experience
Waukesha, WI, 53188

My dog had the BEST weekend away from me!! Dropping my dog at Dana's was like dropping him at the Ritz! Dana was so gracious, welcoming and accommodating- making sure she knew my dog's preferences and comforts. Her two pugs were adorable and Sammy seemed to enjoy having them as playmates! I loved all the pictures and updates. My sporting dog can be a handful but Dana seemed to manage his care with ease and kindness. Her backyard & deck is beautiful. She is a gem of a dog lover! I reside in Illinois. I needed her services while traveling...I may need to pay her to "relocate" ha-ha. Thank you, Dana. My dog transitioned home beautifully. You're the Best!

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Jane Celeste F.
Sitter Profile Image: Deanne D.
Verified Background Check
Deanne D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
268 reviews
130 repeat clients
25 years of experience
Genoa City, WI, 53128

Very thankful to have found such an amazing dog sitter for our extremely energetic Australian Shepherd. We have used Deanne twice now and plan on her being our go to sitter! She updates with pictures and our Pup is always happy and smiling in the photos. Each time our dog has come home tired and happy. Would recommend her and her family to anyone.

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Taylor K.
Sitter Profile Image: Hannah D.
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Hannah D.
Star Sitter
from
$40
per night
5.0 out of 5 stars
78 reviews
23 repeat clients
26 years of experience
Racine, WI, 53402

Hannah and her family are wonderful! We were provided so many updates and pictures during our dogs week long stay with Hannah. We will definitely look to book with her in the future.

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Garrett H.
Sitter Profile Image: Rebecca S.
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Rebecca S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
181 reviews
55 repeat clients
30 years of experience
Town Of Lake, Milwaukee, WI, 53207

Rebecca and her family made sure to make our dog feel right at home. We received 1-2 updates per day with multiple pictures. Would recommend to anyone looking for a sitter for their furbaby!

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Anthony & Taylor D.
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The median cost per night for dog boarding in Wind Lake is $45

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Sitters in Wind Lake average 11
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

If you’re searching for a Wind Lake dog boarding sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, 828 sitters provided dog boarding in Wind Lake. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 92% of Wind Lake dog boarding sitters respond in under an hour.

Sitters who provide dog boarding in Wind Lake have an average of 20 years of experience. Dog boarding sitters with repeat customers have an average of 11 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Wind Lake.

Rover makes it easy to find Wind Lake dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:

  • Dogs of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their sitter’s pets

There are 828 dog boarding sitters in Wind Lake on Rover, so you’re sure to find the perfect match for your dog! In Wind Lake, 86% of sitters offer daily exercise, 97% offer medication administration, and 94% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.