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 wooden cabin with a porch, two chairs, and a door.

1. 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 AU$280
includes taxes & fees
5 Oct - 6 Oct
Tiny Treehouse Cabin | Bluff Woodlands #2
A bunk bed room with a window view, a ceiling fan, and a TV.

2. 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 AU$215
includes taxes & fees
18 Oct - 19 Oct
Ridgetop Retreat Tiny Home, Dakota MN
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 AU$298
includes taxes & fees
5 Oct - 6 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
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 AU$278
includes taxes & fees
5 Oct - 6 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.

5. 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)
"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 AU$413
includes taxes & fees
5 Oct - 6 Oct
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
A living room with a television, sofa, coffee table, and shelves with decorative items.

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 AU$313
includes taxes & fees
5 Oct - 6 Oct
Vintage Lustron Home Piece of History
A patio with two chairs and a table, a fire pit, a wooden fence, and a shed in the background.

7. 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 AU$375
includes taxes & fees
2 Nov - 3 Nov
Parkside Pet Friendly Bungalow
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, (150 reviews)
"Absolutely amazing! So much charm and space…could definitely stay here again!"
United States
Lynn B.
The price is AU$703
includes taxes & fees
5 Oct - 6 Oct
Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN
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 AU$806
includes taxes & fees
5 Oct - 6 Oct
Three Treehouse Cabins in the Bluff Woodlands
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 AU$298
includes taxes & fees
5 Oct - 6 Oct
Tiny Treehouse Cabin | Bluff Woodlands #3
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, (2 reviews)
"Awesome as usual "
United States
Matthew B.
The price is AU$212
includes taxes & fees
5 Oct - 6 Oct
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, (14 reviews)
"Excellent stay. Very relaxing and we caught some fish right off the back of the houseboat!"
United States
Tom B.
The price is AU$398
includes taxes & fees
13 Oct - 14 Oct
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, (46 reviews)
"Brady was very prompt and the stay exceeded expectations We plan to stay again very soon! Thank you, Brady!"
United States
Josias F.
The price is AU$172
includes taxes & fees
8 Oct - 9 Oct
Tamarack Point Homestead
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 charm, Modern updates

Hokah Ohana House: Historic charm, Modern updates
Hokah
10.0 out of 10, Exceptional, (39 reviews)
"Very comfortable and had everything you need to feel at home!"
United States
David R.
The price is AU$264
includes taxes & fees
26 Oct - 27 Oct
Hokah Ohana House: Historic charm, Modern updates
A bedroom with a bed, a nightstand, a lamp, and a window with curtains.

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

Hidden Gem - 1BR/1Bath in Lax WI
Holy Trinity-Longfellow
9.6 out of 10, Exceptional, (18 reviews)
"Our stay was perfect! The host was easy to communicate with and even let us check in early. The place was so cute! The bed was super comfortable and everything looked good and felt clean. Very safe area and neighborhood. Such a bonus to have a restaurant attached to the property! We will for sure stay here again!"
United States
Heather
The price is AU$241
includes taxes & fees
8 Oct - 9 Oct
Hidden Gem - 1BR/1Bath in Lax WI
A wooden deck with a bench, a white door, and hanging flower baskets.

16. 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 AU$233
includes taxes & fees
5 Oct - 6 Oct
The Bungaleau 1 Bedroom House In Cute Rivertown
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, (68 reviews)
"I"
United States
Charlie
The price is AU$248
includes taxes & fees
22 Oct - 23 Oct
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
A beach with a clear sky and calm sea.

18. Studio Condo Near Lake Pepin - King Bed - Dewdrop

Studio Condo Near Lake Pepin - King Bed - Dewdrop
Pepin
8.4 out of 10, Very good, (12 reviews)
"This is our second time staying here. Very enjoyable! "
United States
Avery
The price is AU$297
includes taxes & fees
6 Oct - 7 Oct
Studio Condo Near Lake Pepin - King Bed - Dewdrop
Fun decorations throughout the apartment. Ask us how you can rent the full floor!

19. 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.
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.

20. 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, (119 reviews)
"Great place"
United States
Mark
The price is AU$228
includes taxes & fees
5 Oct - 6 Oct
NEW, NEW, NEW! Wabasha downtown studio113 Pembroke Ave Unit #102
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

GrandStay Hotel & Suites

GrandStay Hotel & Suites

10/10 Excellent
"Great place! Breakfast was disappointing however. Standard stuff, too cold."
James 3-night trip
Posted 8 hours ago
GrandStay Hotel & Suites

Find out more about Winona County

Everything you need to know about Winona County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winona County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Winona County holiday rentals we have chosen for you start as low as AU$228 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Winona County rentals

At Expedia, we put the best Winona County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winona County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.