A river flowing through a forest with autumn-colored trees.

Winona County Holiday Rentals

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Our top choices for Winona County holiday rentals

A bunk bed room with a window view, a ceiling fan, and a TV.

1. Ridgetop Retreat Tiny Home, Dakota MN

Ridgetop Retreat Tiny Home, Dakota MN
Dakota
9.2 out of 10, Wonderful, (11 reviews)
"This is a camper located on a farm. We have a travel trailer so we were prepared for that. A bit surprised of the setting. Our bad, we didn’t realize from the photos that we would be crawling up in a loft to sleep. It was an adventure I guess."
United States
Daniel
The price is HK$847
HK$1,080 total
includes taxes & fees
27 Oct - 28 Oct
Ridgetop Retreat Tiny Home, Dakota MN
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 HK$1,941
HK$2,376 total
includes taxes & fees
27 Oct - 28 Oct
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
A two-story house with a wooden staircase leading to a yellow door, a brick wall, and a window with a white frame.

3. 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, (35 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 HK$1,349
HK$1,708 total
includes taxes & fees
26 Oct - 27 Oct
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
A living room with a television, sofa, coffee table, and shelves with decorative items.

4. 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 HK$1,059
HK$1,680 total
includes taxes & fees
29 Oct - 30 Oct
Vintage Lustron Home Piece of History
A wooden cabin with a porch, a door, and a small seating area with two chairs.

5. Tiny Treehouse Cabin | Bluff Woodlands #2

Tiny Treehouse Cabin | Bluff Woodlands #2
Elba
9.8 out of 10, Exceptional, (17 reviews)
"Beautiful area enjoyed our stay immensely"
United Kingdom
I.M l.
The price is HK$923
HK$1,500 total
includes taxes & fees
26 Oct - 27 Oct
Tiny Treehouse Cabin | Bluff Woodlands #2
A round glass table with two wicker chairs, a bottle, and two glasses of red wine on a metal tray.

6. 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, (152 reviews)
"This was a fabulous place to stay- clean, comfortable, beautiful and accessible."
United States
Ruth S.
The price is HK$2,117
HK$3,585 total
includes taxes & fees
8 Nov - 9 Nov
Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN
A covered deck with outdoor seating, surrounded by a forested area.

7. Tiny Treehouse Cabin | Bluff Woodlands #3

Tiny Treehouse Cabin | Bluff Woodlands #3
Elba
10.0 out of 10, Exceptional, (13 reviews)
"My family of 4 had a wonderful stay!"
United States
Josh S.
The price is HK$1,008
HK$1,591 total
includes taxes & fees
26 Oct - 27 Oct
Tiny Treehouse Cabin | Bluff Woodlands #3
A modern living room with a black door, a grey armchair, a sofa, and a lamp.

8. 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 HK$1,953
HK$2,398 total
includes taxes & fees
2 Nov - 3 Nov
Parkside Pet Friendly Bungalow
A wooden cabin with a porch, two chairs, and a door.

9. Three Tiny Treehouse Cabins in the Bluff Woodlands

Three Tiny Treehouse Cabins in the Bluff Woodlands
Elba
The price is HK$2,939
HK$4,438 total
includes taxes & fees
26 Oct - 27 Oct
Three Tiny Treehouse Cabins in the Bluff Woodlands
Two wooden cabins elevated on stilts in a forest, with outdoor seating and hammocks.

10. Tiny Treehouse Cabin | Bluff Woodlands #1

Tiny Treehouse Cabin | Bluff Woodlands #1
Elba
9.6 out of 10, Exceptional, (10 reviews)
"Great area a place to stay. "
United States
Paul T.
The price is HK$1,008
HK$1,608 total
includes taxes & fees
26 Oct - 27 Oct
Tiny Treehouse Cabin | Bluff Woodlands #1
A spacious living room with a brown sofa, a round coffee table, and a patterned rug. There is a ceiling fan, a dining area with chairs, and a staircase leading to another level.

11. Hokah Ohana House: Historic Apartment Near La Crosse, WI

Hokah Ohana House: Historic Apartment Near La Crosse, WI
Hokah
10.0 out of 10, Exceptional, (40 reviews)
"Very comfortable and had everything you need to feel at home!"
United States
David R.
The price is HK$715
HK$1,611 total
includes taxes & fees
26 Oct - 27 Oct
Hokah Ohana House: Historic Apartment Near La Crosse, WI
Fun decorations throughout the apartment. Ask us how you can rent the full floor!

12. Modern Downtown La Crosse Apartment

Modern Downtown La Crosse Apartment
Historic Downtown La Crosse
9.4 out of 10, Exceptional, (75 reviews)
"Nice, quiet property that's in a great location."
United States
Jacob P.
The price is HK$855
HK$2,877 total
includes taxes & fees
26 Oct - 27 Oct
Modern Downtown La Crosse Apartment
A modern living room with a dark wooden bookshelf, a grey sofa, and a dining area with a wooden chair.

13. NEW, NEW, NEW! Wabasha downtown studio113 Pembroke Ave Unit #102

NEW, NEW, NEW! Wabasha downtown studio113 Pembroke Ave Unit #102
Wabasha
10.0 out of 10, Exceptional, (122 reviews)
"Great place as advertised!"
United States
Timothy
The price is HK$863
HK$1,095 total
includes taxes & fees
9 Nov - 10 Nov
NEW, NEW, NEW! Wabasha downtown studio113 Pembroke Ave Unit #102
55" smart samsung curve tv with sound-bar. Hulu Live included

14. Modern Flat in Downtown La Crosse

Modern Flat in Downtown La Crosse
Historic Downtown La Crosse
9.8 out of 10, Exceptional, (58 reviews)
"The instructions were so well executed so we knew exactly what to do when we arrived and throughout our stay. Great space all around"
United States
Hillary P.
The price is HK$980
HK$3,039 total
includes taxes & fees
26 Oct - 27 Oct
Modern Flat in Downtown La Crosse
A wooden deck with a bench, a white door, and hanging flower baskets.

15. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (107 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is HK$981
HK$1,258 total
includes taxes & fees
27 Oct - 28 Oct
The Bungaleau 1 Bedroom House In Cute Rivertown
A field of lavender with a path leading through it.

16. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (48 reviews)
"Nice quiet getaway."
United States
RICHARD
The price is HK$715
HK$920 total
includes taxes & fees
1 Nov - 2 Nov
Tamarack Point Homestead
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

17. 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, (69 reviews)
"I"
United States
Charlie
The price is HK$941
HK$1,578 total
includes taxes & fees
2 Nov - 3 Nov
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
A bedroom with a bed, bedside table, lamp, and a view of the adjacent room through a wooden-framed door.

18. Spacious 2-bedroom loft above the International Owl Center in Houston, MN

Spacious 2-bedroom loft above the International Owl Center in Houston, MN
Houston
10.0 out of 10, Exceptional, (35 reviews)
"The loft apartment above the International Owl Center was beautiful, spacious, well furnished and very comfortable.Just 3 blocks from the start point of the Root River bike trail, and a short scenic drive away from a variety of outdoor recreation activities and dining options. We had a lovely weekend stay, and were very well supported by the owner. I highly recommend this place for a relaxing or invigorating stay!"
United States
Richard C.
The price is HK$1,953
HK$2,389 total
includes taxes & fees
26 Oct - 27 Oct
Spacious 2-bedroom loft above the International Owl Center in Houston, MN
An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

19. 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 HK$1,059
HK$2,408 total
includes taxes & fees
29 Oct - 30 Oct
Riverfront Twin Home
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

20. Stunning river view loft in Wabasha near Eagle Center

Stunning river view loft in Wabasha near Eagle Center
Wabasha
9.8 out of 10, Exceptional, (91 reviews)
"Really enjoyed the view and amenities, wish we could have stayed longer."
United States
Timothy B.
The price is HK$1,412
HK$2,164 total
includes taxes & fees
26 Oct - 27 Oct
Stunning river view loft in Wabasha near Eagle Center
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 County Hotel Reviews

Country Inn & Suites by Radisson, La Crosse, WI

Country Inn & Suites by Radisson, La Crosse, WI

10/10 Excellent
"The property was very nice! The room was well clean and stocked!"
Keannah 1-night trip
Posted 4 hours ago
Country Inn & Suites by Radisson, La Crosse, WI