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

Search Vacation Homes in Winona

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 ￥23,592
￥29,721 total
includes taxes & fees
Sep 29 - Sep 30
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, (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 ￥36,804
￥42,998 total
includes taxes & fees
Sep 29 - Sep 30
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
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 ￥32,478
￥39,479 total
includes taxes & fees
Sep 30 - Oct 1
Parkside Pet Friendly Bungalow
A wooden deck with a bench, a white door, and hanging flower baskets.

4. 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 ￥19,676
￥25,220 total
includes taxes & fees
Sep 29 - Sep 30
The Bungaleau 1 Bedroom House In Cute Rivertown
A living room with a television, sofa, coffee table, and shelves with decorative items.

5. 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 ￥21,233
￥33,010 total
includes taxes & fees
Sep 29 - Sep 30
Vintage Lustron Home Piece of History
A field of lavender with a path leading through it.

6. 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 ￥14,344
￥18,452 total
includes taxes & fees
Oct 1 - Oct 2
Tamarack Point Homestead
A swimming pool with a water fountain, surrounded by a covered area and trees.

7. 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, (23 reviews)
"Enjoyed our stay in this peaceful, quiet neighborhood."
United States
Colleen C.
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.

8. 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 ￥21,233
￥46,124 total
includes taxes & fees
Sep 29 - Sep 30
Riverfront Twin Home
A modern bar area with a large flat-screen TV displaying a beach scene, wooden cabinets, neon signs, and comfortable seating.

9. Chic Mid-Century 4BR Near UW Campus

Chic Mid-Century 4BR Near UW 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 ￥23,611
￥67,489 total
includes taxes & fees
Sep 29 - Sep 30
Chic Mid-Century 4BR Near UW Campus
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
9.6 out of 10, Exceptional, (104 reviews)
"Comfortable place, beautiful spot!"
United States
Grace D.
The price is ￥25,479
￥30,737 total
includes taxes & fees
Sep 29 - Sep 30
The Hen House Retreat - A Comfortable Place to Roost
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

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, (67 reviews)
"I"
United States
Charlie
The price is ￥15,413
￥26,769 total
includes taxes & fees
Oct 4 - Oct 5
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
A living room with a fireplace, sofas, a TV, and a view of a lake.

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

Riverview, 5BR, Hot tub, Fireplace, Arcade Game
Minneiska
The price is ￥55,677
￥63,668 total
includes taxes & fees
Sep 29 - Sep 30
Riverview, 5BR, Hot tub, Fireplace, Arcade Game
A two-story Victorian-style house with a front porch, a staircase, and a well-maintained lawn.

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, (83 reviews)
"Beautiful place to stay! Very clean and really cool with all the history!"
United States
Robert P.
The price is ￥29,018
￥36,989 total
includes taxes & fees
Sep 30 - Oct 1
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
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 ￥78,640
￥119,968 total
includes taxes & fees
Sep 30 - Oct 1
NEW Mississippi Riverfront Sunset House - family, friends & river come together
A kitchen with wooden cabinets, a granite countertop, a built-in island, and a ceiling with a textured design.

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 ￥102,232
￥121,530 total
includes taxes & fees
Oct 1 - Oct 2
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winona Hotel Reviews

Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

10/10 Excellent
"Friendly staff, quiet environment. My son particularly liked the pool."
Bookman 1-night trip
Posted 1 hour ago
Express Suites Riverport Inn & Suites

Find out more about Winona

Winona Vacation Homes information

Number of reviews
640
Accommodation
95 Vacation Homes
Lowest Price
￥18,452
Highest Price
￥121,530