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

Holiday Homes in Winona

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Winona holiday homes

A two-story house with a wooden staircase leading to a yellow door, a brick wall, and a window with a white frame.

1. 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, (29 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
The price is €168
includes taxes & fees
22 Sept - 23 Sept
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
A modern apartment with a staircase, a dining area, and a living space.

2. 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, (33 reviews)
"A charming place to stay with a spacious primary bedroom, laundry room, and living areas. The backyard patio is a perfect place for a morning coffee and a quiet evening. We would definitely rebook on our next visit."
United States
Mainul
The price is €253
includes taxes & fees
13 Sept - 14 Sept
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
A patio with two chairs and a table, a fire pit, a wooden fence, and a shed in the background.

3. Parkside Pet Friendly Bungalow

Parkside Pet Friendly Bungalow
Winona
The price is €228
includes taxes & fees
23 Sept - 24 Sept
Parkside Pet Friendly Bungalow
A round glass table with two wicker chairs, a bottle, and two glasses of red wine on a metal tray.

4. Charming Brick Farmhouse with a Touch of Elegance. -Winona

Charming Brick Farmhouse with a Touch of Elegance. -Winona
Winona
10.0 out of 10, Exceptional, (147 reviews)
"Absolutely amazing! So much charm and space…could definitely stay here again!"
United States
Lynn B.
The price is €448
includes taxes & fees
17 Sept - 18 Sept
Charming Brick Farmhouse with a Touch of Elegance. -Winona
A field of lavender with a path leading through it.

5. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (45 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveller
The price is €105
includes taxes & fees
20 Sept - 21 Sept
Tamarack Point Homestead
A wooden deck with a bench, a white door, and hanging flower baskets.

6. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (103 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is €142
includes taxes & fees
18 Sept - 19 Sept
The Bungaleau 1 Bedroom House In Cute Rivertown
A living room with a television, sofa, coffee table, and shelves with decorative items.

7. Vintage Lustron Home Piece of History

Vintage Lustron Home Piece of History
Minnesota City
10.0 out of 10, Exceptional, (34 reviews)
"A beautiful comfortable welcoming home!"
United States
Jocelyn R.
The price is €199
includes taxes & fees
21 Sept - 22 Sept
Vintage Lustron Home Piece of History
A dining area with a wooden table and chairs, a kitchen with white cabinets, and two paintings on the wall.

8. The Chateau on Butterfly Trail - 6 Bdrm Retreat

The Chateau on Butterfly Trail - 6 Bdrm Retreat
Fountain City
7.4 out of 10, Good, (3 reviews)
"Thankyou"
United States
Kathy P.
The price is €375
includes taxes & fees
9 Sept - 10 Sept
The Chateau on Butterfly Trail - 6 Bdrm Retreat
An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

9. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (61 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 €266
includes taxes & fees
10 Sept - 11 Sept
Riverfront Twin Home
A modern bar area with a large flat-screen TV displaying a beach scene, wooden cabinets, neon signs, and comfortable seating.

10. Bright 4BR Retreat | UW-La Crosse

Bright 4BR Retreat | UW-La Crosse
Holy Trinity-Longfellow
9.4 out of 10, Exceptional, (43 reviews)
"Walkable to grocery store, gas station and Restraunts which was super helpful since the rental car company was closed when we arrived at the airport due to our flight being delayed.Would definitely stay again"
United States
Kim M.
The price is €372
includes taxes & fees
9 Sept - 10 Sept
Bright 4BR Retreat | UW-La Crosse
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

11. 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, (66 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 €151
includes taxes & fees
23 Sept - 24 Sept
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
A garden with a bench and various plants.

12. 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, (103 reviews)
"Comfortable place, beautiful spot!"
United States
Grace D.
The price is €172
includes taxes & fees
9 Sept - 10 Sept
The Hen House Retreat - A Comfortable Place to Roost
A two-story Victorian-style house with a front porch, a staircase, and a well-maintained lawn.

13. 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, (79 reviews)
"Beautiful place to stay! Very clean and really cool with all the history!"
United States
Robert P.
The price is €206
includes taxes & fees
13 Sept - 14 Sept
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
A living room with a fireplace, sofas, a TV, and a view of a lake.

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

Riverview, 5BR, Hot tub, Fireplace, Arcade Game
Minneiska
The price is €353
includes taxes & fees
9 Sept - 10 Sept
Riverview, 5BR, Hot tub, Fireplace, Arcade Game
A two-story house with a covered patio, a grill, and a well-maintained lawn.

15. 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 €698
includes taxes & fees
29 Sept - 30 Sept
NEW Mississippi Riverfront Sunset House - family, friends & river come together
A kitchen with wooden cabinets, a granite countertop, a built-in island, and a ceiling with a textured design.

16. The Tritsch House -Beautifully Restored Queen Anne Alma WI - Central Air

The Tritsch House -Beautifully Restored Queen Anne Alma WI - Central Air
Alma
10.0 out of 10, Exceptional, (37 reviews)
"Great property!"
United States
MaryJo P.
The price is €725
includes taxes & fees
1 Oct - 2 Oct
The Tritsch House -Beautifully Restored Queen Anne Alma WI - Central Air
A spacious living room with a red sofa, a white coffee table, and a fireplace.

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

Great River Road - Victorian Historic Home (1898)
Fountain City
9.4 out of 10, Exceptional, (11 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 €610
includes taxes & fees
14 Sept - 15 Sept
Great River Road - Victorian Historic Home (1898)
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

Stoney Creek Hotel La Crosse - Onalaska

Stoney Creek Hotel La Crosse - Onalaska

8/10 Good
"It's consistently great here. Sometimes the payment process with debit cards is rocky, but they work with you easily"
Kari 2-night trip
Posted less than an hour ago
Stoney Creek Hotel La Crosse - Onalaska

Find out more about Winona

Winona Holiday Homes information

Number of reviews
799
Accommodation
95 Holiday Homes
Lowest Price
€105
Highest Price
€725