A stone wall with a hole, overlooking a river and a town.

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winona vacation homes

Interior

1. Charming 3-bedroom, 2 bathroom house with outdoor space in Winona

Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Winona
10.0 out of 10, Exceptional, (31 reviews)
"This charming home was perfect for our girls weekend. The home was very clean and offered great accommodations. We would love to stay here again!"
United States
Jenna M.
The price is ￥37,265
￥45,936 total
includes taxes & fees
Aug 12 - Aug 13
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Exterior detail

2. Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons

Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
Historic Downtown Winona
10.0 out of 10, Exceptional, (28 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
The price is ￥23,888
￥30,436 total
includes taxes & fees
Aug 12 - Aug 13
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
Property grounds

3. Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater

Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater
Winona
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful property- there were so many fun things to do and loved the location."
United States
Sean J.
The price is ￥50,020
￥109,538 total
includes taxes & fees
Aug 16 - Aug 17
Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater
Terrace/patio

4. Parkside Pet Friendly Bungalow

Parkside Pet Friendly Bungalow
Winona
The price is ￥33,073
￥40,867 total
includes taxes & fees
Sep 1 - Sep 2
Parkside Pet Friendly Bungalow
Living area

5. Great River Road - Victorian Historic Home (1898)

Great River Road - Victorian Historic Home (1898)
Fountain City
9.2 out of 10, Wonderful, (9 reviews)
"We had an amazing 3 nights here. It’s a beautiful, cozy house with so much room for cooking and visiting family !"
United States
amy r.
The price is ￥71,663
￥111,391 total
includes taxes & fees
Aug 24 - Aug 25
Great River Road - Victorian Historic Home (1898)
Smart TV, books

6. Vintage Lustron Home Piece of History

Vintage Lustron Home Piece of History
Minnesota City
10.0 out of 10, Exceptional, (34 reviews)
"I loved staying here! The interior was comfortable, cozy, and fascinating! "
United States
melanie
The price is ￥27,518
￥41,785 total
includes taxes & fees
Aug 25 - Aug 26
Vintage Lustron Home Piece of History
Terrace/patio

7. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (101 reviews)
"Awesome!"
United States
Logan
The price is ￥19,922
￥25,536 total
includes taxes & fees
Aug 12 - Aug 13
The Bungaleau 1 Bedroom House In Cute Rivertown
Property grounds

8. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (42 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveler
The price is ￥14,524
￥18,684 total
includes taxes & fees
Aug 16 - Aug 17
Tamarack Point Homestead
Exterior

9. NEW Mississippi Riverfront Sunset House - family, friends & river come together

NEW Mississippi Riverfront Sunset House - family, friends & river come together
Buffalo City
10.0 out of 10, Exceptional, (5 reviews)
"great experience !!"
United States
pamela m.
The price is ￥103,513
￥158,434 total
includes taxes & fees
Sep 1 - Sep 2
NEW Mississippi Riverfront Sunset House - family, friends & river come together
Game room

10. The Chateau on Butterfly Trail - 6 Bdrm Retreat

The Chateau on Butterfly Trail - 6 Bdrm Retreat
Fountain City
2.0 out of 10, (1 review)
"My family and I went there for the holiday weekend, we get there full of Dust, extremely dirty. Dead ladybugs in drawers, Windows sills, spider webs, refrigerator not functioning well was leaking. Was very dissapointed with the pictures vs. Reality. Do not recommend."
United States
ALFREDO M.
The price is ￥51,425
￥71,855 total
includes taxes & fees
Sep 1 - Sep 2
The Chateau on Butterfly Trail - 6 Bdrm Retreat
Property grounds

11. The Hen House Retreat - A Comfortable Place to Roost

The Hen House Retreat - A Comfortable Place to Roost
Highland
9.6 out of 10, Exceptional, (100 reviews)
"Very nice perfect for us, would rent again!"
United States
Mitchell G.
The price is ￥25,799
￥31,636 total
includes taxes & fees
Aug 18 - Aug 19
The Hen House Retreat - A Comfortable Place to Roost
Outdoor dining

12. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (56 reviews)
"Great property! Enjoyed the property and outdoor space was amazing! While there is not conventional central air, the space stayed cool."
United States
Melissa
The price is ￥21,499
￥49,266 total
includes taxes & fees
Aug 16 - Aug 17
Riverfront Twin Home
Property grounds

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

Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Northside
9.8 out of 10, Exceptional, (65 reviews)
"This place has so much personality and charm! We loved our stay, so many fun little details to enjoy. Very easily accessible to the downtown area, which made our experience very smooth. We'd love to stay there again the next time we're in La Crosse."
United States
Colin W.
The price is ￥15,607
￥27,105 total
includes taxes & fees
Aug 21 - Aug 22
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Smart TV, fireplace, books

14. Riverview, 5BR, Hot tub, Fireplace, Arcade Game

Riverview, 5BR, Hot tub, Fireplace, Arcade Game
Minneiska
The price is ￥56,375
￥67,545 total
includes taxes & fees
Aug 13 - Aug 14
Riverview, 5BR, Hot tub, Fireplace, Arcade Game
Exterior

15. Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Historic Downtown La Crosse
9.8 out of 10, Exceptional, (75 reviews)
"Great communication with hostBeautiful historic home. Wonderful place to stay with a group. "
United States
Melissa W.
The price is ￥29,382
￥38,736 total
includes taxes & fees
Aug 20 - Aug 21
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Exterior

16. Downtown Boho Home w/Office, Yoga Studio,King Bed

Downtown Boho Home w/Office, Yoga Studio,King Bed
Holy Trinity-Longfellow
9.6 out of 10, Exceptional, (7 reviews)
"Super cute home. Worked out great for our family of four. "
United States
Jenny N.
The price is ￥31,683
￥71,749 total
includes taxes & fees
Aug 12 - Aug 13
Downtown Boho Home w/Office, Yoga Studio,King Bed
Interior

17. Sunny Mid-Century 4BR | Near UW

Sunny Mid-Century 4BR | Near UW
Holy Trinity-Longfellow
9.4 out of 10, Exceptional, (41 reviews)
"Lovely atmosphere- great location. It was perfect for our family getaway to visit our son in college."
United States
Lynn M.
The price is ￥23,907
￥72,364 total
includes taxes & fees
Aug 12 - Aug 13
Sunny Mid-Century 4BR | Near UW
Living area

18. Farmhouse Apartment - River Road Historic Home

Farmhouse Apartment - River Road Historic Home
Fountain City
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful property with views of the Mississippi. Host checked in on us often and was very accommodating. We really enjoyed reading about the history of the home. There were so many cute details including a framed print of the original house plans. Nice place to stay."
United States
Heather O.
The price is ￥21,499
￥36,459 total
includes taxes & fees
Aug 24 - Aug 25
Farmhouse Apartment - River Road Historic Home
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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Top Winona Hotel Reviews

Country Inn & Suites by Radisson, La Crosse, WI

Country Inn & Suites by Radisson, La Crosse, WI

8/10 Good
"All good"
Mark 2-night trip
Posted 6 hours ago
Country Inn & Suites by Radisson, La Crosse, WI

Find out more about Winona

Winona Vacation Homes information

Number of reviews
449
Accommodation
95 Vacation Homes
Lowest Price
￥18,684
Highest Price
￥158,434