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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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
10.0 out of 10, Exceptional, (34 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
The price is AU$312
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 AU$415
includes taxes & fees
25 Oct - 26 Oct
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
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 AU$373
includes taxes & fees
2 Nov - 3 Nov
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. 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 AU$695
includes taxes & fees
18 Oct - 19 Oct
Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN
A field of lavender with a path leading through it.

5. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (46 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveller
The price is AU$172
includes taxes & fees
18 Oct - 19 Oct
Tamarack Point Homestead
A living room with a television, sofa, coffee table, and shelves with decorative items.

6. 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.
Vintage Lustron Home Piece of History
A wooden deck with a bench, a white door, and hanging flower baskets.

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, (105 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is AU$234
includes taxes & fees
27 Oct - 28 Oct
The Bungaleau 1 Bedroom House In Cute Rivertown
A room with bunk beds, a bedside table with a lamp, a dresser with drawers, a window with curtains, and a bed with patterned bedding.

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 AU$729
includes taxes & fees
19 Oct - 20 Oct
The Chateau on Butterfly Trail - 6 Bdrm Retreat
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

9. 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 AU$256
includes taxes & fees
22 Oct - 23 Oct
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
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)
"Comfortable place, beautiful spot!"
United States
Grace D.
The price is AU$289
includes taxes & fees
28 Oct - 29 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 AU$595
includes taxes & fees
18 Oct - 19 Oct
Riverview, 5BR, Hot tub, Fireplace, Arcade Game
A swimming pool with a water fountain, surrounded by a covered area and trees.

12. French Island w/Hot Tub, Kayak, Lake View, EV

French Island w/Hot Tub, Kayak, Lake View, EV
La Crosse
9.8 out of 10, Exceptional, (24 reviews)
"Enjoyed our stay in this peaceful, quiet neighborhood."
United States
Colleen C.
The price is AU$445
includes taxes & fees
20 Oct - 21 Oct
French Island w/Hot Tub, Kayak, Lake View, EV
An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

13. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (65 reviews)
"Perfect place for a quick weekend getaway"
United States
Jack H.
The price is AU$434
includes taxes & fees
18 Oct - 19 Oct
Riverfront Twin Home
A two-story house with a covered patio, a grill, and a well-maintained lawn.

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, (6 reviews)
"great experience !!"
United States
pamela m.
The price is AU$1,123
includes taxes & fees
1 Nov - 2 Nov
NEW Mississippi Riverfront Sunset House - family, friends & river come together
A modern bar area with a large flat-screen TV displaying a beach scene, wooden cabinets, neon signs, and comfortable seating.

15. Vintage Gem Near College & Downtown

Vintage Gem Near College & Downtown
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.
Vintage Gem Near College & Downtown
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

8/10 Good
"Close to the hospital. Good food at the bistro. Breakfast was good. View of Target was dismal but definitely a walkable location"
Kathryn 1-night trip
Posted 4 hours ago
Express Suites Riverport Inn & Suites

Find out more about Winona

Winona Holiday Homes information

Number of reviews
619
Accommodation
98 Holiday Homes
Lowest Price
AU$172
Highest Price
AU$1,123