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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winona vacation 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, (32 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
The price is ￥23,678
￥29,998 total
includes taxes & fees
Oct 28 - Oct 29
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)
"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 ￥36,937
￥45,191 total
includes taxes & fees
Oct 8 - Oct 9
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 ￥34,311
￥42,209 total
includes taxes & fees
Oct 5 - Oct 6
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, (150 reviews)
"Absolutely amazing! So much charm and space…could definitely stay here again!"
United States
Lynn B.
The price is ￥46,224
￥78,761 total
includes taxes & fees
Oct 4 - Oct 5
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)
"Brady was very prompt and the stay exceeded expectations We plan to stay again very soon! Thank you, Brady!"
United States
Josias F.
The price is ￥14,396
￥18,519 total
includes taxes & fees
Oct 8 - Oct 9
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, (105 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is ￥19,747
￥25,311 total
includes taxes & fees
Oct 4 - Oct 5
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 ￥21,310
￥33,809 total
includes taxes & fees
Oct 12 - Oct 13
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.
The price is ￥21,310
￥37,138 total
includes taxes & fees
Oct 14 - Oct 15
Farmhouse Apartment - River Road Historic Home
A brick fireplace with a flat-screen TV above it, surrounded by potted plants and a leather couch.

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 ￥54,465
￥93,014 total
includes taxes & fees
Oct 4 - Oct 5
The Chateau on Butterfly Trail - 6 Bdrm Retreat
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

10. 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, (68 reviews)
"I"
United States
Charlie
The price is ￥14,403
￥25,652 total
includes taxes & fees
Oct 4 - Oct 5
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
A garden with a bench and various plants.

11. 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, (104 reviews)
"Comfortable place, beautiful spot!"
United States
Grace D.
The price is ￥25,572
￥31,526 total
includes taxes & fees
Oct 4 - Oct 5
The Hen House Retreat - A Comfortable Place to Roost
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, (62 reviews)
"Perfect place for a quick weekend getaway"
United States
Jack H.
The price is ￥21,334
￥48,161 total
includes taxes & fees
Oct 11 - Oct 12
Riverfront Twin Home
A living room with a fireplace, sofas, a TV, and a view of a lake.

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

Riverview, 5BR, Hot tub, Fireplace, Arcade Game
Minneiska
The price is ￥55,879
￥66,951 total
includes taxes & fees
Oct 20 - Oct 21
Riverview, 5BR, Hot tub, Fireplace, Arcade Game
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, (5 reviews)
"great experience !!"
United States
pamela m.
The price is ￥78,925
￥128,397 total
includes taxes & fees
Nov 1 - Nov 2
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. Bluff View Haven | Steps to Campus

Bluff View Haven | Steps to Campus
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 ￥20,287
￥67,263 total
includes taxes & fees
Oct 8 - Oct 9
Bluff View Haven | Steps to Campus
A two-story Victorian-style house with a front porch, a staircase, and a well-maintained lawn.

16. 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, (84 reviews)
"Beautiful place to stay! Very clean and really cool with all the history!"
United States
Robert P.
The price is ￥29,123
￥37,123 total
includes taxes & fees
Oct 12 - Oct 13
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
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 ￥72,295
￥115,740 total
includes taxes & fees
Oct 13 - Oct 14
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

Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

8/10 Good
"The property was very good and the staff was very helpful. We enjoyed the stay. We would not hesitate to stay here again."
Louise 1-night trip
Posted 3 hours ago
Express Suites Riverport Inn & Suites

Find out more about Winona

Winona Vacation Homes information

Number of reviews
801
Accommodation
95 Vacation Homes
Lowest Price
￥18,519
Highest Price
￥128,397