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

Vacation Rentals in Winona County

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Top Cities in Winona County

A large brick building with a central dome and arched windows, surrounded by green grass and trees.
Vacation RentalsVacation Rentals

Minnesota City

Minnesota City

Our top choices for Winona County vacation 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
9.4 out of 10, Exceptional, (10 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 ￥16,648
￥21,237 total
includes taxes & fees
Sep 10 - Sep 11
Ridgetop Retreat Tiny Home, Dakota MN
A wooden cabin with a porch, two chairs, and a door.

2. Tiny Treehouse Cabin | Bluff Woodlands #2

Tiny Treehouse Cabin | Bluff Woodlands #2
Elba
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful area enjoyed our stay immensely"
United Kingdom
I.M l.
The price is ￥18,096
￥29,402 total
includes taxes & fees
Sep 11 - Sep 12
Tiny Treehouse Cabin | Bluff Woodlands #2
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
10.0 out of 10, Exceptional, (29 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
The price is ￥23,058
￥29,213 total
includes taxes & fees
Oct 5 - Oct 6
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
A covered deck with outdoor seating, surrounded by a forested area.

4. 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 ￥19,756
￥31,354 total
includes taxes & fees
Sep 13 - Sep 14
Tiny Treehouse Cabin | Bluff Woodlands #3
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, (35 reviews)
"A beautiful comfortable welcoming home!"
United States
Jocelyn R.
The price is ￥22,827
￥35,487 total
includes taxes & fees
Sep 21 - Sep 22
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, (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 ￥35,970
￥44,008 total
includes taxes & fees
Sep 20 - Sep 21
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
A round glass table with two wicker chairs, a bottle, and two glasses of red wine on a metal tray.

7. Charming Brick Farmhouse with a Touch of Elegance. -Winona

Charming Brick Farmhouse with a Touch of Elegance. -Winona
Winona
10.0 out of 10, Exceptional, (147 reviews)
"Absolutely amazing! So much charm and space…could definitely stay here again!"
United States
Lynn B.
The price is ￥49,251
￥82,139 total
includes taxes & fees
Sep 17 - Sep 18
Charming Brick Farmhouse with a Touch of Elegance. -Winona
A patio with two chairs and a table, a fire pit, a wooden fence, and a shed in the background.

8. Parkside Pet Friendly Bungalow

Parkside Pet Friendly Bungalow
Winona
The price is ￥33,105
￥40,769 total
includes taxes & fees
Sep 23 - Sep 24
Parkside Pet Friendly Bungalow
A wooden cabin with a porch, two chairs, and a door.

9. Three Treehouse Cabins in the Bluff Woodlands

Three Treehouse Cabins in the Bluff Woodlands
Elba
The price is ￥57,608
￥86,982 total
includes taxes & fees
Sep 13 - Sep 14
Three 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, (9 reviews)
"Great area a place to stay. "
United States
Paul T.
The price is ￥19,756
￥31,520 total
includes taxes & fees
Sep 10 - Sep 11
Tiny Treehouse Cabin | Bluff Woodlands #1
A compact RV kitchen with wooden cabinets, a stove, and a dining area with a bench.

11. Big River Escape Coyote Camper #1

Big River Escape Coyote Camper #1
Buffalo City
10.0 out of 10, Exceptional, (1 review)
"Awesome as usual "
United States
Matthew B.
The price is ￥18,139
￥22,380 total
includes taxes & fees
Sep 14 - Sep 15
Big River Escape Coyote Camper #1
A calm river with boats docked on the right, a clear sky, and dense trees on the left.

12. 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, (10 reviews)
"Being our first experience lodging on a house boat, we felt as though we were staying in luxury. Unexpectedly, the boat was fully equipped with everything. The owner has it tastefully decorated, neat and very clean. Good location and within walking of a couple popular bar/restaurant eateries, although many around the city (college town). The welcome notebook inside the boat explains everything, with contact information. We fished each day off the boat using our own gear, unfortunately, not...
United States
Paula
The price is ￥23,934
￥41,307 total
includes taxes & fees
Oct 6 - Oct 7
2-bedroom house boat in beautiful La Crosse with AC comfort
A field of lavender with a path leading through it.

13. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (45 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveler
The price is ￥14,019
￥18,034 total
includes taxes & fees
Sep 13 - Sep 14
Tamarack Point Homestead
A wooden deck with a bench, a white door, and hanging flower baskets.

14. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (103 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is ￥19,230
￥24,649 total
includes taxes & fees
Sep 18 - Sep 19
The Bungaleau 1 Bedroom House In Cute Rivertown

15. Riverfront Cabin with Private Dock

Riverfront Cabin with Private Dock
Buffalo City
10.0 out of 10, Exceptional, (5 reviews)
"Great place!!!"
United States
Cynthia B.
The price is ￥20,134
￥24,484 total
includes taxes & fees
Sep 15 - Sep 16
Riverfront Cabin with Private Dock
A wooden cabin interior with a sofa, dining table, chairs, kitchen area, and a ceiling fan.

16. Turtle Cabin Near Mississippi River

Turtle Cabin Near Mississippi River
Buffalo City
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful area, friendly locals. Perfect place to stay for aome family time! We can't wait to come back!"
United States
Sarah M.
The price is ￥20,497
￥24,869 total
includes taxes & fees
Sep 10 - Sep 11
Turtle Cabin Near Mississippi River
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.

17. Hokah Ohana House: Historic charm, Modern updates

Hokah Ohana House: Historic charm, Modern updates
Hokah
10.0 out of 10, Exceptional, (38 reviews)
"Host very responsive, the accommodations were impeccably clean, great location and the layout was perfect for families!"
United States
Dia F.
The price is ￥12,887
￥27,778 total
includes taxes & fees
Sep 13 - Sep 14
Hokah Ohana House: Historic charm, Modern updates
A bedroom with a bed, a nightstand, a lamp, and a window with curtains.

18. Hidden Gem - 1BR/1Bath in Lax WI

Hidden Gem - 1BR/1Bath in Lax WI
Holy Trinity-Longfellow
9.6 out of 10, Exceptional, (17 reviews)
"Lovely property in a great area. Would absolutely stay here again!"
United States
Karen H.
The price is ￥16,755
￥25,456 total
includes taxes & fees
Sep 17 - Sep 18
Hidden Gem - 1BR/1Bath in Lax WI
A small blue shed with a white door, a patio with a table and chairs, and a wooden fence with plants.

19. 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, (46 reviews)
"Wonderful property and great host!"
United States
Anonymous traveler
The price is ￥19,369
￥29,842 total
includes taxes & fees
Sep 15 - Sep 16
The Alton House - Come experience tiny house living in beautiful Pepin!
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
"!"
Igor 1-night trip
Posted 4 hours ago
Country Inn & Suites by Radisson, La Crosse, WI

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Vacation Apartments in Winona County

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