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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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, (36 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 NZ$380
includes taxes & fees
23 Nov - 24 Nov
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 NZ$520
includes taxes & fees
5 Nov - 6 Nov
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, (153 reviews)
"This was a fabulous place to stay- clean, comfortable, beautiful and accessible."
United States
Ruth S.
The price is NZ$776
includes taxes & fees
9 Nov - 10 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 NZ$474
includes taxes & fees
1 Nov - 2 Nov
Parkside Pet Friendly Bungalow
A wooden deck with a bench, a white door, and hanging flower baskets.

5. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (108 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is NZ$285
includes taxes & fees
5 Nov - 6 Nov
The Bungaleau 1 Bedroom House In Cute Rivertown
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.
The price is NZ$398
includes taxes & fees
16 Nov - 17 Nov
Vintage Lustron Home Piece of History
A rural landscape with a barn, a small house, and a large house with a porch.

7. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (48 reviews)
"Nice quiet getaway."
United States
RICHARD
The price is NZ$222
includes taxes & fees
2 Nov - 3 Nov
Tamarack Point Homestead
A spacious living room with a stone fireplace, leather furniture, and a large window providing natural light.

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 NZ$964
includes taxes & fees
1 Nov - 2 Nov
The Chateau on Butterfly Trail - 6 Bdrm Retreat
A two-story house with a covered porch, a small garden with yellow flowers, and a bird feeder.

9. 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, (109 reviews)
"We enjoyed our stay. Thank you for the clean property and well described property."
United States
Lydia F.
The price is NZ$347
includes taxes & fees
1 Nov - 2 Nov
The Hen House Retreat - A Comfortable Place to Roost
A living room with a fireplace, sofas, a TV, and a view of a lake.

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

Riverview, 5BR, Hot tub, Fireplace, Arcade Game
Minneiska
The price is NZ$764
includes taxes & fees
12 Nov - 13 Nov
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.

11. 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 NZ$538
includes taxes & fees
30 Oct - 31 Oct
Riverfront Twin Home
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

12. 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, (71 reviews)
"Liked the retro decor, outdoor gazebo, firepit and location."
United States
Tim
The price is NZ$339
includes taxes & fees
2 Nov - 3 Nov
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
A swimming pool with a water fountain, surrounded by a covered area and trees.

13. 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, (25 reviews)
"Enjoyed our stay in this peaceful, quiet neighborhood."
United States
Colleen C.
The price is NZ$549
includes taxes & fees
3 Nov - 4 Nov
French Island w/Hot Tub, Kayak, Lake View, EV
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 NZ$886
includes taxes & fees
1 Nov - 2 Nov
Campus-Area 4BR | Panoramic Bluffs
A two-story Victorian-style house with a front porch, a staircase, and a well-maintained lawn.

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, (88 reviews)
"Beautiful place to stay! Very clean and really cool with all the history!"
United States
Robert P.
The price is NZ$418
includes taxes & fees
3 Nov - 4 Nov
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

Holiday Inn Express & Suites Winona by IHG

Holiday Inn Express & Suites Winona by IHG

10/10 Excellent
"Great property in an excellent location. Very accommodating and clean."
DOMINIC 2-night trip
Posted 8 hours ago
Holiday Inn Express & Suites Winona by IHG

Find out more about Winona

Winona Holiday Homes information

Number of reviews
627
Accommodation
80 Holiday Homes
Lowest Price
NZ$222
Highest Price
NZ$964