Dog Boarding Winona

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Over 191
pet parents in Winona have booked dog boarding

Winona, 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: Rebekah L.
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Rebekah L.
Star Sitter
from
$60
per night
5.0 out of 5 stars
34 reviews
15 repeat clients
6 years of experience
Winona, MN, 55987

Rebekah was great! Lots of playtime and walks. Blaze had a great time. Also appreciated photos and updates. I felt very comfortable leaving her even though it was her first time there. Woukd definitely go back again. Thanks so much!

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Carrie P.
Sitter Profile Image: Destiny S.
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Destiny S.
from
$35
per night
5.0 out of 5 stars
13 reviews
3 repeat clients
10 years of experience
Fountain City, WI, 54629

Destiny was absolutely amazing with my dog. She entered pictures and ask questions when needed. My dog will be going back to her and her family any time I need a sitter!!

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Mindy S.
Sitter Profile Image: Erica & Ciara M.
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Erica & Ciara M.
from
$50
per night
4.8 out of 5 stars
39 reviews
20 repeat clients
15 years of experience
Winona, MN, 55987

Couldn’t recommend Erica and Ciara enough!! It was my first time boarding my dog and was really anxious about it. They were great with keeping me updated and sending pics, and also very patient with my dog, who was very worked up since it was her first time away from home. I am so thankful for the care they provided!!

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Tara H.
Sitter Profile Image: Erica K.
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Erica K.
from
$40
per night
5.0 out of 5 stars
119 reviews
24 repeat clients
12 years of experience
Winona, MN, 55987

Erica is absolutely amazing! Loved getting pictures and videos everyday Charlie was there. Charlie had so much fun he didn’t want to get in the car to come home! Would highly recommend her!!

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Adam S.
Sitter Profile Image: Ty E.
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Ty E.
Star Sitter
from
$45
per night
5.0 out of 5 stars
275 reviews
85 repeat clients
20 years of experience
LA CRESCENT, MN, 55947

Millie loved her time at Ty’s! She doesn’t always like to eat when given the opportunity to play with other dogs, but Ty worked with her and was able to get her to eat her meals:)

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Stephanie D.
Sitter Profile Image: William L.
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William L.
Star Sitter
from
$42
per night
5.0 out of 5 stars
48 reviews
14 repeat clients
35 years of experience
Holmen, WI, 54636

We were needing last minute dog sitting and Bill was gracious enough to watch our pup. He was accommodating and provided updates for us. Our pup had a great time!

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Elizabeth M.
Sitter Profile Image: Laura L.
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Laura L.
from
$32
per night
5.0 out of 5 stars
9 reviews
1 repeat client
50 years of experience
Holmen, WI, 54636

Laura sent pictures and updates. My dog was very well cared for. I will be using her services in the future.

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William L.
Sitter Profile Image: Jenny H.
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Jenny H.
Star Sitter
from
$40
per night
5.0 out of 5 stars
31 reviews
6 repeat clients
10 years of experience
La Crosse, WI, 54603

Jenny was the best sitter I’ve ever met on Rover, hands down! She gave me regular updates about my pup and sent me tons of photos. I never needed to worry about my dog; Jenny always made sure I knew how he was doing. Will absolutely book her again!!

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Rachel I.
Sitter Profile Image: Alicia G.
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Alicia G.
from
$50
per night
5.0 out of 5 stars
118 reviews
16 repeat clients
33 years of experience
Winona, MN, 55987

Alicia is great. Ollie loves going to see her and he always comes home tuckered out. Dogs get plenty of play time, walks, dog parks etc. Highly recommend using her.

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Brent S.
Sitter Profile Image: Angela D.
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Angela D.
Star Sitter
from
$50
per night
4.9 out of 5 stars
38 reviews
12 repeat clients
12 years of experience
Onalaska, WI, 54650

Angela was awesome, super friendly, and she took great care of our baby Lucy while we were away. Would definitely recommend, and we will book her again.

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Jason B.
Sitter Profile Image: Susan P.
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Susan P.
from
$48
per night
5.0 out of 5 stars
3 reviews
2 repeat clients
18 years of experience
La Crosse, WI, 54601

Susan was the perfect sitter for my Shiba Inu! She took good care of him, took him on multiple walks, and even baked him dog treats! Plus she’s a delightful person who’s easy to coordinate with. I can’t recommend her highly enough!!!

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Sarah M.
Sitter Profile Image: Megan P.
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Megan P.
from
$55
per night
5.0 out of 5 stars
5 reviews
1 repeat client
25 years of experience
Winona, MN, 55987

Megan took great care of my dog and even taught her how to (finally) use the stairs! ? Fantastic sitter!

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Allison M.
Sitter Profile Image: Nadia V.
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Nadia V.
from
$38
per night
5.0 out of 5 stars
17 reviews
5 repeat clients
16 years of experience
Minneiska, MN, 55910

Nadia took such excellent care of our dog! She sent us pictures and gave us updates throughout the weekend, which I greatly appreciated! Would definitely recommend her and would use her to care for our dog again in the future!

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Andrea J.
Sitter Profile Image: Jared Z.
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Jared Z.
from
$30
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
8 years of experience
Onalaska, WI, 54650

Jared was very helpful and accommodating. Princess was well taken care of and had a lot of cuddles from everyone in the family. I will contact again next time I need a sitter for Princess!

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Angela D.
Sitter Profile Image: Megan F.
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Megan F.
from
$50
per night
5.0 out of 5 stars
4 reviews
10 years of experience
St. Charles, MN, 55972

Megan did a great job watching our dog while we were on vacation. I appreciate the quick response and pictures throughout our trip.

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Alyssa A.
Sitter Profile Image: Aj D.
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Aj D.
from
$55
per night
4.7 out of 5 stars
12 reviews
1 repeat client
25 years of experience
La Crosse, WI, 54603

Great communication and our dog was very happy upon our return! Would definitely recommend!

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Augusta W.
Sitter Profile Image: Karlie G.
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Karlie G.
Star Sitter
from
$50
per night
5.0 out of 5 stars
29 reviews
9 repeat clients
8 years of experience
West Salem, WI, 54669

Karlie took great care of my pup during his stay. He got along well with her dog as well. They got a lot of both play and nap time together! He also came home with a cute bandana! (Thanks again for that). She is responsive, kind and truly loves to care for animals.

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Latyrin B.
Sitter Profile Image: Luke S.
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Luke S.
from
$45
per night
4.7 out of 5 stars
13 reviews
6 repeat clients
15 years of experience
La Crosse, WI, 54601

About: While living in Seattle I worked for Rover doing dog boarding in my own home, at times with up to five dogs at a time. Currently I am not available to do dog boarding in my own home however I would love to take your fur babies on a walk Only able to service the city limits of La Crosse, Onalaska, and La Cresent I would be more than happy to watch your animals at your home. I do my best to respect your family and your belongings while I am in your home.

Sitter Profile Image: Justine O.
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Justine O.
from
$40
per night
5.0 out of 5 stars
1 review
10 years of experience
Lewiston, MN, 55952

About: I have always been an avid animal-lover. From childhood into adulthood, I have owned and cared for a variety of pets, including dogs, cats, small mammals, reptiles, birds & fish. My family & I currently share our home with two dogs, a bearded dragon, a Russian tortoise, & a ball python. I have several years of professional work experience in animal care (zoo, kennel care, walking, basic grooming) and wildlife / parks & recreation—both of which are relevant. I enjoy the outdoors and keeping all of our furry (& scaly) friends happy. I will board dogs, small mammals, reptiles & birds in my home! Upon request, I can do drop-in visits for cats or exotic animals within a 15 mile radius. I am currently a stay-at-home mom & so my schedule allows me to be at home majority of the time. If I need to leave the house, it’s never for more than a couple of hours. I have a large four-story home, which provides amble space for pets to play or to be separated if need be. I utilize crates for dogs who need or prefer it. Our yard is unfenced, so I use slip leads and tie-out cables for potty time.

Sitter Profile Image: Tyonna G.
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Tyonna G.
from
$35
per night
4.3 out of 5 stars
4 reviews
2 repeat clients
5 years of experience
La Crosse, WI, 54603

About: I’ve taken care of dogs for as long as I can remember. From dogs to cats, and teacup sized to waist size. Dog and cats are treated like babies with me, so your fur will always be in good paws! i’m currently working part time but I have plenty of time for your fur babies! Weekdays, weekends… mornings, nights whenever you need me I’ll be there. I have a fenced yard with plenty of room to run and play and I also have four other dogs, they can easily be put into a different room if you don’t feel comfortable with them socializing!

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The median cost per night for dog boarding in Winona is $40

Dog parents share their Rover experiences - Winona

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5.0 out of 5 stars

Rebekah took wonderful care of our senior dog. Gave him lots of fun and love and her home has a great set up for dogs. She was great about communication and following feeding and meds instructions. It was wonderful to enjoy our weekend knowing our Sven was in such caring, capable hands.

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Lizz B.
Boarding
5.0 out of 5 stars

Gemma is always so very happy to see and stay with Lynne! I NEVER worry about her as I know she gets the best care with Lynne!

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Julie G.
Boarding
5.0 out of 5 stars

Naomi took care of my dog like her own. She communicated well when I was away and made my weekend away comfortable know my dog was with her.

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Andy B.
Boarding
5.0 out of 5 stars

Good communication, and appreciated flexibility around some last minute changes to drop off and pick up timing.

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Brian M.
Boarding
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Popular requests for dog boarding - Winona

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Sitters in Winona average 8
repeat dog boarding clients

FAQs for Boarding - Winona

Frequently asked questions about Rover

The average cost for Dog Boarding in Winona on Rover is $35.31 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 82 sitters on Rover offering Dog Boarding across Winona. Enter your ZIP code to see which available sitters are closest to your home.

Every sitter 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.

Sitters may also include daily walks in the neighborhood during your dog's boarding stay. You can also request photo and message updates throughout so you can see which local 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 Winona 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 Winona.

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 Winona 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 MN 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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