Search Holiday Homes in Winona

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Winona holiday homes

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, (37 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
The price is £157
includes taxes & fees
23 Nov - 24 Nov
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons

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, (36 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 £218
includes taxes & fees
15 Nov - 16 Nov
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona

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 £319
includes taxes & fees
15 Nov - 16 Nov
Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN

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 £180
includes taxes & fees
30 Nov - 1 Dec
Parkside Pet Friendly Bungalow

5. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (49 reviews)
"Nice quiet getaway."
United States
RICHARD
The price is £90
includes taxes & fees
24 Nov - 25 Nov
Tamarack Point Homestead

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 £155
includes taxes & fees
16 Nov - 17 Nov
Vintage Lustron Home Piece of History

7. 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 £381
includes taxes & fees
15 Nov - 16 Nov
The Chateau on Butterfly Trail - 6 Bdrm Retreat

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

Riverview, 5BR, Hot tub, Fireplace, Arcade Game
Minneiska
The price is £308
includes taxes & fees
2 Dec - 3 Dec
Riverview, 5BR, Hot tub, Fireplace, Arcade Game

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, (110 reviews)
"We enjoyed our stay. Thank you for the clean property and well described property."
United States
Lydia F.
The price is £142
includes taxes & fees
15 Nov - 16 Nov
The Hen House Retreat - A Comfortable Place to Roost

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, (73 reviews)
"Liked the retro decor, outdoor gazebo, firepit and location."
United States
Tim
The price is £139
includes taxes & fees
16 Nov - 17 Nov
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

11. 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 £224
includes taxes & fees
15 Nov - 16 Nov
French Island w/Hot Tub, Kayak, Lake View, EV

12. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (66 reviews)
"Great place to stay for a weekend of fishing."
United States
Jason K.
The price is £222
includes taxes & fees
18 Nov - 19 Nov
Riverfront Twin Home

13. Chic Mid-Century 4BR Near UW Campus

Chic Mid-Century 4BR Near UW Campus
Holy Trinity-Longfellow
9.6 out of 10, Exceptional, (46 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 £359
includes taxes & fees
18 Nov - 19 Nov
Chic Mid-Century 4BR Near UW Campus

14. 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, (89 reviews)
"Beautiful place to stay! Very clean and really cool with all the history!"
United States
Robert P.
The price is £166
includes taxes & fees
16 Nov - 17 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.

Learn more about Winona

Nestled between dramatic bluffs along the Mississippi River, this historic town offers vibrant arts festivals and excellent hiking through Sugar Loaf's trails. Visit the Minnesota Marine Art Museum to see masterpieces, then rent kayaks to explore hidden backwaters when summer temperatures peak.

A lake with a rocky hill and trees in the foreground.

Top reviews in Winona