Book Holiday Homes in Winona

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Featured Holiday Homes in Winona

River Front Property

River Front Property

La Crosse
With a stay at this vacation home, you'll be centrally located in La Crosse, a 4-minute drive from Mississippi River and 7 minutes from La Crosse Center.
River Front Property
Mississippi waterfront vacation home that welcomes dogs! Private dock for boats

Mississippi waterfront vacation home that welcomes dogs! Private dock for boats

2 out of 5
Brownsville
When you stay at this vacation home in Brownsville, you'll be 1 minutes by foot from Mississippi River.
Mississippi waterfront vacation home that welcomes dogs! Private dock for boats
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

La Crosse
The price is AU$401 per night from 20 Mar to 21 Mar
AU$401
includes taxes & fees
20 Mar - 21 Mar
With a stay at this vacation home in La Crosse, you'll be within a 15-minute walk of University of Wisconsin-La Crosse and La Crosse Center.
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
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8th Street Blues!  3 Bed, 2 Bath near downtown LaCrosse

8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

La Crosse
With a stay at this vacation home, you'll be centrally located in La Crosse, within a 5-minute drive of La Crosse Center and University of Wisconsin-La ...
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse
Charming 3-bedroom house with WiFi and AC in beautiful La Crosse

Charming 3-bedroom house with WiFi and AC in beautiful La Crosse

La Crosse
With a stay at this vacation home in La Crosse, you'll be within a 15-minute drive of University of Wisconsin-La Crosse and La Crosse Center.
Charming 3-bedroom house with WiFi and AC in beautiful La Crosse
Charming 2-bedroom house on the Bay

Charming 2-bedroom house on the Bay

La Crosse
With a stay at this vacation home in La Crosse, you'll be within a 10-minute drive of La Crosse Center and University of Wisconsin-La Crosse.
Charming 2-bedroom house on the Bay
Within walking distance of all the amenities!  Bike the trail~ float the river

Within walking distance of all the amenities! Bike the trail~ float the river

Lanesboro
A stay at this vacation home places you in the heart of Lanesboro, steps from Lanesboro Historical Museum and Lanesboro Arts Center.
Within walking distance of all the amenities! Bike the trail~ float the river
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

Winona
With a stay at this vacation home, you'll be centrally located in Winona, within a 5-minute walk of Mississippi River and Watkins Heritage Museum.
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO
Enjoy this newly remodeled house located on Lake Onalaska.

Enjoy this newly remodeled house located on Lake Onalaska.

Onalaska
With a stay at this vacation home in Onalaska, you'll be on the waterfront, within a 15-minute drive of Mississippi River and Great River Trail.
Enjoy this newly remodeled house located on Lake Onalaska.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Winona Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winona vacation homes are the perfect way for you to wing it.

Holiday houses in Winona let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winona in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winona adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winona with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winona vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winona Holiday Homes essential information

Accommodation
91 Holiday Homes
Lowest Price
AU$105
Highest Price
AU$401
Popular accommodation
River Front Property , Mississippi waterfront vacation home that welcomes dogs! Private dock for boats, Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion, 8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse, Charming 3-bedroom house with WiFi and AC in beautiful La Crosse, Charming 2-bedroom house on the Bay, Within walking distance of all the amenities! Bike the trail~ float the river, Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO, Enjoy this newly remodeled house located on Lake Onalaska.

Top trending hotels in Winona

Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

3 out of 5
900 Bruski Dr, Winona, MN
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 9 Mar to 10 Mar
AU$193
includes taxes & fees
9 Mar - 10 Mar
With a stay at Express Suites Riverport Inn & Suites, you'll be centrally located in Winona, within a 5-minute drive of Mississippi River and Lake Park.
Express Suites Riverport Inn & Suites
AmericInn by Wyndham Winona

AmericInn by Wyndham Winona

2.5 out of 5
303 Pelzer Street, Winona, MN
Fully refundableReserve now, pay when you stay
The price is AU$205 per night from 16 Mar to 17 Mar
AU$205
includes taxes & fees
16 Mar - 17 Mar
Located in Winona, AmericInn by Wyndham Winona is in a rural location, within a 5-minute drive of St. Mary's University of Minnesota and Minnesota Marine Art ...
AmericInn by Wyndham Winona
Super 8 by Wyndham Winona MN

Super 8 by Wyndham Winona MN

2 out of 5
1025 Sugar Loaf Rd, Winona, MN
Fully refundableReserve now, pay when you stay
The price is AU$105 per night from 16 Mar to 17 Mar
AU$105
includes taxes & fees
16 Mar - 17 Mar
Located in Winona, Super 8 by Wyndham Winona MN is in a rural location, within a 15-minute walk of Sugar Loaf Trailhead and Winona Health.
Super 8 by Wyndham Winona MN
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The Plaza Hotel & Suites Winona

The Plaza Hotel & Suites Winona

3 out of 5
1025 Highway 61 E, Winona, MN
Fully refundableReserve now, pay when you stay
The price is AU$211 per night from 9 Mar to 10 Mar
AU$211
includes taxes & fees
9 Mar - 10 Mar
Located in Winona, The Plaza Hotel & Suites Winona is within a 15-minute walk of Lake Park and Sugar Loaf.
The Plaza Hotel & Suites Winona
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.