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

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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, (32 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
The price is £146
includes taxes & fees
30 Sept - 1 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, (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 £205
includes taxes & fees
27 Sept - 28 Sept
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 £186
includes taxes & fees
27 Sept - 28 Sept
Parkside Pet Friendly Bungalow
A field of lavender with a path leading through it.

4. 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 £91
includes taxes & fees
1 Oct - 2 Oct
Tamarack Point Homestead
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 £160
includes taxes & fees
4 Oct - 5 Oct
Vintage Lustron Home Piece of History
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 £123
includes taxes & fees
27 Sept - 28 Sept
The Bungaleau 1 Bedroom House In Cute Rivertown
An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

7. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (62 reviews)
"Great property! Enjoyed the property and outdoor space was amazing! While there is not conventional central air, the space stayed cool."
United States
Melissa
The price is £232
includes taxes & fees
29 Sept - 30 Sept
Riverfront Twin Home
A swimming pool with a water fountain, surrounded by a covered area and trees.

8. 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.
The price is £240
includes taxes & fees
28 Sept - 29 Sept
French Island w/Hot Tub, Kayak, Lake View, EV
A garden with a bench and various plants.

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, (104 reviews)
"Comfortable place, beautiful spot!"
United States
Grace D.
The price is £149
includes taxes & fees
27 Sept - 28 Sept
The Hen House Retreat - A Comfortable Place to Roost
A modern bar area with a large flat-screen TV displaying a beach scene, wooden cabinets, neon signs, and comfortable seating.

10. 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 £323
includes taxes & fees
27 Sept - 28 Sept
Chic Mid-Century 4BR Near UW Campus
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 £131
includes taxes & fees
4 Oct - 5 Oct
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
A two-story Victorian-style house with a front porch, a staircase, and a well-maintained lawn.

12. 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, (81 reviews)
"Beautiful place to stay! Very clean and really cool with all the history!"
United States
Robert P.
The price is £179
includes taxes & fees
30 Sept - 1 Oct
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
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 £307
includes taxes & fees
28 Sept - 29 Sept
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 £605
includes taxes & fees
29 Sept - 30 Sept
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 £615
includes taxes & fees
1 Oct - 2 Oct
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.
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Top Winona Hotel Reviews

GrandStay Hotel & Suites

GrandStay Hotel & Suites

8/10 Good
"Decent stay, but had a perfume go missing... The 1 bed apartment was spacious and had everything you need. There was confusion / conflicting messages abotu whether housekeeping was available or not (some said yes, some said no, some said not on weekends), but either way had the room cleaned on both nights. Breakfast was ok. I also had a perfume go missing after a housekeeping visit. When I informed the front desk the response was "oh no, we'll call you if we find it". I sent a message to the hotel after I checked out too about the issue, and still haven't heard back."
Sabrina 3-night trip
Posted 4 hours ago
GrandStay Hotel & Suites

Find out more about Winona

Winona Holiday Homes information

Number of reviews
638
Accommodation
97 Holiday Homes
Lowest Price
£91
Highest Price
£615