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

Exterior detail

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, (30 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
The price is NZ$325
includes taxes & fees
22 Sept - 23 Sept
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
Interior

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 NZ$494
includes taxes & fees
14 Sept - 15 Sept
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Terrace/patio

3. Parkside Pet Friendly Bungalow

Parkside Pet Friendly Bungalow
Winona
10.0 out of 10, Exceptional, (1 review)
"Parkview is a quaint bungalow one block off the Lake. Easy access to Downtown, Winona State and recreation. Lovely back yard and front porch. Plenty of party in front and back. Definitely will stay again."
United States
Mary T.
The price is NZ$439
includes taxes & fees
14 Sept - 15 Sept
Parkside Pet Friendly Bungalow
Living area

4. Vintage Lustron Home Piece of History

Vintage Lustron Home Piece of History
Minnesota City
10.0 out of 10, Exceptional, (35 reviews)
"A beautiful comfortable welcoming home!"
United States
Jocelyn R.
The price is NZ$384
includes taxes & fees
21 Sept - 22 Sept
Vintage Lustron Home Piece of History
Property grounds

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 NZ$202
includes taxes & fees
17 Sept - 18 Sept
Tamarack Point Homestead
Terrace/patio

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 NZ$276
includes taxes & fees
18 Sept - 19 Sept
The Bungaleau 1 Bedroom House In Cute Rivertown
Living area

7. 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 NZ$1,221
includes taxes & fees
14 Sept - 15 Sept
Great River Road - Victorian Historic Home (1898)
Outdoor dining

8. 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 NZ$522
includes taxes & fees
20 Sept - 21 Sept
Riverfront Twin Home
Interior

9. Campus-Area 4BR | Panoramic Bluffs

Campus-Area 4BR | Panoramic Bluffs
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 NZ$775
includes taxes & fees
14 Sept - 15 Sept
Campus-Area 4BR | Panoramic Bluffs
Property grounds

10. 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 NZ$340
includes taxes & fees
14 Sept - 15 Sept
The Hen House Retreat - A Comfortable Place to Roost
Property grounds

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 NZ$293
includes taxes & fees
12 Oct - 13 Oct
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Living area

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

Riverview, 5BR, Hot tub, Fireplace, Arcade Game
Minneiska
The price is NZ$717
includes taxes & fees
14 Sept - 15 Sept
Riverview, 5BR, Hot tub, Fireplace, Arcade Game
Exterior

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, (80 reviews)
"Beautiful place to stay! Very clean and really cool with all the history!"
United States
Robert P.
The price is NZ$414
includes taxes & fees
15 Sept - 16 Sept
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Exterior

14. 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 NZ$1,341
includes taxes & fees
29 Sept - 30 Sept
NEW Mississippi Riverfront Sunset House - family, friends & river come together
Private kitchen

15. 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, (38 reviews)
"Great property!"
United States
MaryJo P.
The price is NZ$1,365
includes taxes & fees
1 Oct - 2 Oct
The Tritsch House -Beautifully Restored Queen Anne Alma WI - Central Air
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

GrandStay Hotel & Suites

GrandStay Hotel & Suites

10/10 Excellent
"Room was very spacious and clean. But, the carpet has seen better days and the bottom was coming out of the top dresser drawer."
Jeff 2-night trip
Posted 15 hours ago
GrandStay Hotel & Suites

Find out more about Winona

Winona Holiday Homes information

Number of reviews
586
Accommodation
97 Holiday Homes
Lowest Price
NZ$202
Highest Price
NZ$1,365