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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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
9.8 out of 10, Exceptional, (35 reviews)
"We really enjoyed staying at the house. It was very clean and comfortable. All the little things were done right; well stocked, labeled, and nicely decorated. We’re staying here again when we come back to Winona."
United States
Dan F.
The price is €200
includes taxes & fees
26 Oct - 27 Oct
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, (34 reviews)
"Great little home for a girls getaway. Perfect size for 3 people and enjoyed our time together and exploring Winona!"
United States
Nicole H.
The price is €274
includes taxes & fees
25 Oct - 26 Oct
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
A round glass table with two wicker chairs, a bottle, and two glasses of red wine on a metal tray.

3. Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN

Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN
Winona
10.0 out of 10, Exceptional, (152 reviews)
"Absolutely amazing! So much charm and space…could definitely stay here again!"
United States
Lynn B.
The price is €418
includes taxes & fees
2 Nov - 3 Nov
Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN
A modern living room with a black door, a grey armchair, a sofa, and a lamp.

4. Parkside Pet Friendly Bungalow

Parkside Pet Friendly Bungalow
Winona
8.0 out of 10, Very good, (2 reviews)
"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 €272
includes taxes & fees
2 Nov - 3 Nov
Parkside Pet Friendly Bungalow
A field of lavender with a path leading through it.

5. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (48 reviews)
"Nice quiet getaway."
United States
RICHARD
The price is €109
includes taxes & fees
25 Oct - 26 Oct
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, (106 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is €147
includes taxes & fees
25 Oct - 26 Oct
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, (36 reviews)
"A beautiful comfortable welcoming home!"
United States
Jocelyn R.
The price is €196
includes taxes & fees
29 Oct - 30 Oct
Vintage Lustron Home Piece of History
A spacious living room with a red sofa, a white coffee table, and a fireplace.

8. Farmhouse Apartment - River Road Historic Home

Farmhouse Apartment - River Road Historic Home
Fountain City
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful views, excellent location near several cute towns, plus Winona, which has lots of chain store shopping options. The trains were barely noticeable, personally I like the sound. Definitely recommend!"
United States
Katie B.
Farmhouse Apartment - River Road Historic Home
A neatly made bed with a plaid bedspread, a bedside table with a lamp, and two framed pictures on the wall.

9. 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 €567
includes taxes & fees
27 Oct - 28 Oct
The Chateau on Butterfly Trail - 6 Bdrm Retreat
A garden with a bench and various plants.

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

The Hen House Retreat - A Comfortable Place to Roost
Highland
9.8 out of 10, Exceptional, (106 reviews)
"We enjoyed our stay. Thank you for the clean property and well described property."
United States
Lydia F.
The price is €178
includes taxes & fees
26 Oct - 27 Oct
The Hen House Retreat - A Comfortable Place to Roost
A living room with a fireplace, sofas, a TV, and a view of a lake.

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

Riverview, 5BR, Hot tub, Fireplace, Arcade Game
Minneiska
The price is €378
includes taxes & fees
27 Oct - 28 Oct
Riverview, 5BR, Hot tub, Fireplace, Arcade Game
An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

12. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (66 reviews)
"Perfect place for a quick weekend getaway"
United States
Jack H.
The price is €279
includes taxes & fees
29 Oct - 30 Oct
Riverfront Twin Home
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

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, (69 reviews)
"I"
United States
Charlie
The price is €186
includes taxes & fees
2 Nov - 3 Nov
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
A modern bar area with a large flat-screen TV displaying a beach scene, wooden cabinets, neon signs, and comfortable seating.

14. Campus-Area 4BR | Panoramic Bluffs

Campus-Area 4BR | Panoramic Bluffs
Holy Trinity-Longfellow
9.6 out of 10, Exceptional, (45 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 €429
includes taxes & fees
26 Oct - 27 Oct
Campus-Area 4BR | Panoramic Bluffs
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, (6 reviews)
"great experience !!"
United States
pamela m.
The price is €723
includes taxes & fees
3 Nov - 4 Nov
NEW Mississippi Riverfront Sunset House - family, friends & river come together
A spacious living room with a red sofa, a white coffee table, and a fireplace.

16. 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.
Great River Road - Victorian Historic Home (1898)
A two-story Victorian-style house with a front porch, a staircase, and a well-maintained lawn.

17. 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, (87 reviews)
"Beautiful place to stay! Very clean and really cool with all the history!"
United States
Robert P.
The price is €214
includes taxes & fees
26 Oct - 27 Oct
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
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

Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

10/10 Excellent
"Loved the big lobby, swimming pool, hot tub, bed and shower were both great. The bar restaurant had good food."
Paula 4-night trip
Posted 4 hours ago
Express Suites Riverport Inn & Suites

Find out more about Winona

Winona Holiday Homes information

Number of reviews
621
Accommodation
95 Holiday Homes
Lowest Price
€109
Highest Price
€723