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

Holiday Rentals in Winona County

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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)
"Everything was perfect for our one night stay… owner was very helpful and easy to reach. Only small issue was that it was a little difficult to get up and down the ladders to the lofted beds.. but now that we know what to expect, we would definitely consider staying here again!"
United States
Jessica W.
The price is €127
includes taxes & fees
27 Oct - 28 Oct
Ridgetop Retreat Tiny Home, Dakota MN
A wooden cabin with a porch, a door, and a small seating area with two chairs.

2. 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 €178
includes taxes & fees
25 Oct - 26 Oct
Tiny Treehouse Cabin | Bluff Woodlands #2
Two wooden cabins elevated on stilts in a forest, with outdoor seating and hammocks.

3. 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 €190
includes taxes & fees
25 Oct - 26 Oct
Tiny Treehouse Cabin | Bluff Woodlands #1
A two-story house with a wooden staircase leading to a yellow door, a brick wall, and a window with a white frame.

4. 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 €200
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.

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 €211
includes taxes & fees
24 Nov - 25 Nov
Vintage Lustron Home Piece of History
A modern apartment with a staircase, a dining area, and a living space.

6. 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 €274
includes taxes & fees
25 Oct - 26 Oct
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
A wooden cabin with a porch, two chairs, and a door.

7. Three Tiny Treehouse Cabins in the Bluff Woodlands

Three Tiny Treehouse Cabins in the Bluff Woodlands
Elba
The price is €494
includes taxes & fees
25 Oct - 26 Oct
Three Tiny Treehouse Cabins in the Bluff Woodlands
A round glass table with two wicker chairs, a bottle, and two glasses of red wine on a metal tray.

8. 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)
"Absolutely amazing! So much charm and space…could definitely stay here again!"
United States
Lynn B.
The price is €459
includes taxes & fees
24 Nov - 25 Nov
Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN
A modern living room with a black door, a grey armchair, a sofa, and a lamp.

9. 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 €272
includes taxes & fees
2 Nov - 3 Nov
Parkside Pet Friendly Bungalow
A covered deck with outdoor seating, surrounded by a forested area.

10. 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 €190
includes taxes & fees
25 Oct - 26 Oct
Tiny Treehouse Cabin | Bluff Woodlands #3
A calm river with boats docked on the right, a clear sky, and dense trees on the left.

11. 2-bedroom house boat in beautiful La Crosse with AC comfort

2-bedroom house boat in beautiful La Crosse with AC comfort
West La Crosse
10.0 out of 10, Exceptional, (16 reviews)
"Excellent stay. Very relaxing and we caught some fish right off the back of the houseboat!"
United States
Tom B.
2-bedroom house boat in beautiful La Crosse with AC comfort
A field of lavender with a path leading through it.

12. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (48 reviews)
"Nice quiet getaway."
United States
RICHARD
The price is €109
includes taxes & fees
25 Oct - 26 Oct
Tamarack Point Homestead
A wooden deck with a bench, a white door, and hanging flower baskets.

13. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (106 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is €147
includes taxes & fees
5 Nov - 6 Nov
The Bungaleau 1 Bedroom House In Cute Rivertown
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.

14. 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 €188
includes taxes & fees
26 Oct - 27 Oct
Hokah Ohana House: Historic Apartment Near La Crosse, WI
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

15. 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 €186
includes taxes & fees
2 Nov - 3 Nov
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
A modern living room with a dark wooden bookshelf, a grey sofa, and a dining area with a wooden chair.

16. 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 €129
includes taxes & fees
9 Nov - 10 Nov
NEW, NEW, NEW! Wabasha downtown studio113 Pembroke Ave Unit #102
Fun decorations throughout the apartment. Ask us how you can rent the full floor!

17. 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 €330
includes taxes & fees
26 Oct - 27 Oct
Modern Downtown La Crosse Apartment
A small blue shed with a white door, a patio with a table and chairs, and a wooden fence with plants.

18. The Alton House - Come experience tiny house living in beautiful Pepin!

The Alton House - Come experience tiny house living in beautiful Pepin!
Pepin
9.8 out of 10, Exceptional, (54 reviews)
"The tiny home was perfect for our 4-day stay in Pepin. Very cozy and quaint. It had everything we needed. We definitely will stay here again if we're ever find ourselves back in Pepin."
United States
Ranell
The price is €178
includes taxes & fees
26 Oct - 27 Oct
The Alton House - Come experience tiny house living in beautiful Pepin!
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 €279
includes taxes & fees
29 Oct - 30 Oct
Riverfront Twin Home
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

Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

8/10 Good
"it’s good"
Ty 1-night trip
Posted 4 hours ago
Express Suites Riverport Inn & Suites

Find out more about Winona County

Holiday Homes in Winona County

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