A stone wall with a hole, overlooking a river and a town.

Winona Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Winona holiday rentals

Interior

1. 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 HK$1,835
HK$2,161 total
includes taxes & fees
16 Sept - 17 Sept
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Terrace/patio

2. Parkside Pet Friendly Bungalow

Parkside Pet Friendly Bungalow
Winona
10.0 out of 10, Exceptional, (1 review)
"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$1,619
HK$1,994 total
includes taxes & fees
14 Sept - 15 Sept
Parkside Pet Friendly Bungalow
Exterior detail

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, (30 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
The price is HK$1,176
HK$1,490 total
includes taxes & fees
23 Sept - 24 Sept
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
Smart TV, books

4. 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 HK$1,150
HK$1,795 total
includes taxes & fees
22 Sept - 23 Sept
Vintage Lustron Home Piece of History
Living area

5. Great River Road - Victorian Historic Home (1898)

Great River Road - Victorian Historic Home (1898)
Fountain City
9.4 out of 10, Exceptional, (11 reviews)
"We had an amazing 3 nights here. It’s a beautiful, cozy house with so much room for cooking and visiting family !"
United States
amy r.
The price is HK$3,529
HK$5,676 total
includes taxes & fees
14 Sept - 15 Sept
Great River Road - Victorian Historic Home (1898)
Terrace/patio

6. 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 HK$981
HK$1,188 total
includes taxes & fees
18 Sept - 19 Sept
The Bungaleau 1 Bedroom House In Cute Rivertown
Dining

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 HK$1,789
HK$3,449 total
includes taxes & fees
14 Sept - 15 Sept
The Chateau on Butterfly Trail - 6 Bdrm Retreat
2 bedrooms, iron/ironing board, WiFi, bed sheets

8. 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, (29 reviews)
"Host was very attentive and available if needed but everything was perfect. The woodwork is amazing and grand piano sounded like you were in a concert hall. We absolutely loved our stay and hope to make it back since it is such a beautiful area."
United States
Nikki W.
The price is HK$1,953
HK$2,389 total
includes taxes & fees
21 Sept - 22 Sept
Spacious 2-bedroom loft above the International Owl Center in Houston, MN
Property grounds

9. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (45 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveller
The price is HK$715
HK$920 total
includes taxes & fees
17 Sept - 18 Sept
Tamarack Point Homestead
Exterior

10. NEW Mississippi Riverfront Sunset House - family, friends & river come together

NEW Mississippi Riverfront Sunset House - family, friends & river come together
Buffalo City
10.0 out of 10, Exceptional, (5 reviews)
"great experience !!"
United States
pamela m.
The price is HK$3,921
HK$6,379 total
includes taxes & fees
29 Sept - 30 Sept
NEW Mississippi Riverfront Sunset House - family, friends & river come together
Interior

11. 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 HK$847
HK$1,080 total
includes taxes & fees
16 Sept - 17 Sept
Ridgetop Retreat Tiny Home, Dakota MN
Interior

12. River Eagle Cabin #1 w/ Screened Porch & Fire Pit

River Eagle Cabin #1 w/ Screened Porch & Fire Pit
Buffalo City
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay. The cabin was beautiful and the property charming and a great view of the river. Really great location to run along the river if you are a runner!"
United States
Tracy R.
The price is HK$1,555
HK$1,789 total
includes taxes & fees
7 Oct - 8 Oct
River Eagle Cabin #1 w/ Screened Porch & Fire Pit
Terrace/patio

13. 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 HK$923
HK$1,500 total
includes taxes & fees
14 Sept - 15 Sept
Tiny Treehouse Cabin | Bluff Woodlands #2
Coffee/tea maker, fridge, microwave, oven

14. 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 HK$925
HK$1,142 total
includes taxes & fees
14 Sept - 15 Sept
Big River Escape Coyote Camper #1
Coffee/tea maker, fridge, microwave, oven

15. The Tritsch House -Beautifully Restored Queen Anne Alma WI - Central Air

The Tritsch House -Beautifully Restored Queen Anne Alma WI - Central Air
Alma
10.0 out of 10, Exceptional, (38 reviews)
"Great property!"
United States
MaryJo P.
The price is HK$5,098
HK$6,497 total
includes taxes & fees
1 Oct - 2 Oct
The Tritsch House -Beautifully Restored Queen Anne Alma WI - Central Air
Interior

16. Badger Cabin w/ Lofts, Fireplace & WiFi

Badger Cabin w/ Lofts, Fireplace & WiFi
Buffalo City
10.0 out of 10, Exceptional, (1 review)
"The cabin was adorable. Greg was great! The cabin was spotless. Great water pressure. It rained and it was lovely with the tin roof:) The tv reception was good and the wi - fi was great. Loved it!"
United States
Sharon M.
The price is HK$1,203
HK$1,443 total
includes taxes & fees
14 Sept - 15 Sept
Badger Cabin w/ Lofts, Fireplace & WiFi
Exterior

17. 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 HK$1,018
HK$1,239 total
includes taxes & fees
14 Sept - 15 Sept
Riverfront Cabin with Private Dock
Smart TV, fireplace, books

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

Riverview, 5BR, Hot tub, Fireplace, Arcade Game
Minneiska
The price is HK$2,776
HK$3,309 total
includes taxes & fees
14 Sept - 15 Sept
Riverview, 5BR, Hot tub, Fireplace, Arcade Game
Property grounds

19. 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$1,608 total
includes taxes & fees
14 Sept - 15 Sept
Tiny Treehouse Cabin | Bluff Woodlands #3
Terrace/patio

20. Three Treehouse Cabins in the Bluff Woodlands

Three Treehouse Cabins in the Bluff Woodlands
Elba
The price is HK$2,939
HK$4,438 total
includes taxes & fees
14 Sept - 15 Sept
Three Treehouse Cabins in the Bluff Woodlands
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 Hotel Reviews

Radisson Hotel La Crosse

Radisson Hotel La Crosse

10/10 Excellent
"Staff was great. The food in the restaurant was amazing. View was perfect over the river. Very pleased with my stay here."
Micah 5-night trip
Posted 4 hours ago
Radisson Hotel La Crosse

Find out more about Winona

Search for holiday rentals in Winona on Expedia! You can easily find your home rentals, villas, holiday apartments in Winona using one of the methods below:

  • View our selection of featured holiday rentals in Winona
  • Use the map to find apartments and other holiday homes in the Winona neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winona while they last

Look no further and take a look at our great range of rental properties in Winona!

Frequently asked questions

Can I find holiday rentals in Winona?

Yes, there are holiday rentals in Winona close to Valencia Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. The riverfront and museums are just a few reasons why tourists like Winona. Make sure you have time to check out the gardens and churches during your trip.

What are some of the best holiday rentals that Winona has to offer?

The Hen House Retreat - A Comfortable Place to Roost: This holiday home rental outside of Winona is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Winona?

Expedia has 13 holiday rentals for your stay in Winona.

What can I see and do in Winona?

Enjoy the outdoors at Lake Park and Sugar Loaf Bluff, or simply take in cultural attractions like Minnesota Marine Art Museum and Winona County Historical Society. While here, Great River Bluffs State Park and Mississippi River are other places worth a visit.

What are holiday rentals like in Winona?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winona. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for families.