Book Holiday Homes in Winona

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Featured Holiday Homes in Winona

Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

La Crosse WI
The price is NZ$273 per night from 24 Mar to 25 Mar
NZ$273
24 Mar - 25 Mar
includes taxes & fees
Stay at this holiday home in La Crosse. Enjoy free Wi-Fi, patios and an in-room coffee maker. Popular attractions Riverside Amusement Park and Shenanigans Entertainment ...
Opens in a new windowNostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
River Front Property

River Front Property

La Crosse WI
Stay at this holiday home in La Crosse. Enjoy free Wi-Fi, a garden and patios. Popular attractions Black River Beach and Shenanigans Entertainment Center & Sports ...
Opens in a new windowRiver Front Property
Cozy 2-bedroom house with country charm and close to everything!

Cozy 2-bedroom house with country charm and close to everything!

Onalaska WI
Stay at this holiday home in Holmen. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Great River Trail and Lost Island Wine are located ...
Opens in a new windowCozy 2-bedroom house with country charm and close to everything!
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Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

La Crosse WI
The price is NZ$410 per night from 22 Mar to 23 Mar
NZ$410
22 Mar - 23 Mar
includes taxes & fees
Stay at this holiday home in La Crosse. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Swarthout Museum and Children's Museum ...
Opens in a new windowComfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Riverfront Twin Home

Riverfront Twin Home

La Crosse WI
The price is NZ$527 per night from 22 Mar to 23 Mar
NZ$527
22 Mar - 23 Mar
includes taxes & fees
Stay at this holiday home in La Crosse. Enjoy laundry facilities, patios and in-room fireplaces. Popular attractions City Brewery and Mary of the Angels Chapel ...
Opens in a new windowRiverfront Twin Home
Beautiful Bay views at Bayfront Resort

Beautiful Bay views at Bayfront Resort

La Crosse WI
Stay at this ski holiday home in La Crosse. Enjoy ski-in/ski-out access and air conditioning. Popular attractions Black River Beach and Shenanigans Entertainment ...
Opens in a new windowBeautiful Bay views at Bayfront Resort
Newly remodeled home in quiet neighborhood

Newly remodeled home in quiet neighborhood

La Crosse WI
Stay at this ski holiday home in La Crosse. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Grandad Bluff Park and St. Rose of Viterbo ...
Opens in a new windowNewly remodeled home in quiet neighborhood
8th Street Blues!  3 Bed, 2 Bath near downtown LaCrosse

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

La Crosse WI
Stay at this family-friendly holiday home in La Crosse. Enjoy a garden, laundry facilities and patios. Popular attractions Mary of the Angels Chapel and St. ...
Opens in a new window8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse
Mississippi River View with updated driveway

Mississippi River View with updated driveway

Altura MN
Stay at this holiday home in Altura. Enjoy laundry facilities, a pool table and patios. Popular attractions John Latsch State Park and Prairie Moon Sculpture ...
Opens in a new windowMississippi River View with updated driveway
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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
98 Holiday Homes
Lowest Price
NZ$114
Highest Price
NZ$527
Popular accommodation
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard, River Front Property , Cozy 2-bedroom house with country charm and close to everything!, Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion, Riverfront Twin Home , Beautiful Bay views at Bayfront Resort, Newly remodeled home in quiet neighborhood, 8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse, Mississippi River View with updated driveway

Top trending hotels in 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 NZ$114 per night from 29 Mar to 30 Mar
NZ$114
29 Mar - 30 Mar
includes taxes & fees
Stay at this business-friendly hotel in Winona. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowSuper 8 by Wyndham Winona MN
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 NZ$171 per night from 23 Mar to 24 Mar
NZ$171
23 Mar - 24 Mar
includes taxes & fees
Stay at this business-friendly hotel in Winona. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
Opens in a new windowExpress Suites Riverport Inn & Suites
Holiday Inn Express & Suites Winona by IHG

Holiday Inn Express & Suites Winona by IHG

2.5 out of 5
1128 Homer Rd Winona MN
Fully refundable
The price is NZ$215 per night from 5 Apr to 6 Apr
NZ$215
5 Apr - 6 Apr
includes taxes & fees
Stay at this family-friendly hotel in Winona. Enjoy free breakfast, free parking and a 24-hour fitness centre. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowHoliday Inn Express & Suites Winona by IHG
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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 NZ$239 per night from 22 Mar to 23 Mar
NZ$239
22 Mar - 23 Mar
includes taxes & fees
Stay at this hotel in Winona. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the pool and the helpful staff in their reviews. Popular attractions ...
Opens in a new windowThe 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.