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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winona holiday rentals

A two-story house with a wooden staircase leading to a yellow door, a brick wall, and a window with a white frame.

1. 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, (36 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
27 Oct - 28 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.

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
26 Oct - 27 Oct
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.

3. 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 modern living room with a black door, a grey armchair, a sofa, and a lamp.

4. 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$1,916
HK$2,357 total
includes taxes & fees
2 Nov - 3 Nov
Parkside Pet Friendly Bungalow
A field of lavender with a path leading through it.

5. 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 wooden deck with a bench, a white door, and hanging flower baskets.

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, (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 living room with a television, sofa, coffee table, and shelves with decorative items.

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

8. 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 wooden cabin with a porch, a door, and a small seating area with two chairs.

9. 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 wooden cabin with a balcony, string lights, and outdoor furniture.

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 HK$1,008
HK$1,591 total
includes taxes & fees
26 Oct - 27 Oct
Tiny Treehouse Cabin | Bluff Woodlands #3
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
A wooden dock extending over a calm water body, surrounded by greenery and a small building.

12. Fox Cabin Near Mississippi River & Trails

Fox Cabin Near Mississippi River & Trails
Buffalo City
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay and really enjoyed the screened in porch. Spent a lot of time sitting at the table in the screened in porch playing cards."
United States
Jenny D.
The price is HK$1,684
HK$2,033 total
includes taxes & fees
7 Nov - 8 Nov
Fox Cabin Near Mississippi River & Trails
A wooden cabin interior with a dining table, chairs, a refrigerator, a stove, and a ladder leading to a loft.

13. 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$1,453
HK$1,756 total
includes taxes & fees
29 Oct - 30 Oct
Badger Cabin w/ Lofts, Fireplace & WiFi
Exterior

14. 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$1,148
HK$1,384 total
includes taxes & fees
16 Nov - 17 Nov
Riverfront Cabin with Private Dock
A neatly made bed with a plaid bedspread, a bedside table with a lamp, and two framed pictures on the wall.

15. 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$2,476
HK$4,336 total
includes taxes & fees
27 Oct - 28 Oct
The Chateau on Butterfly Trail - 6 Bdrm Retreat
Fun decorations throughout the apartment. Ask us how you can rent the full floor!

16. 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 garden with a bench and various plants.

17. The Hen House Retreat - A Comfortable Place to Roost

The Hen House Retreat - A Comfortable Place to Roost
Highland
9.8 out of 10, Exceptional, (107 reviews)
"We enjoyed our stay. Thank you for the clean property and well described property."
United States
Lydia F.
The price is HK$1,270
HK$1,566 total
includes taxes & fees
26 Oct - 27 Oct
The Hen House Retreat - A Comfortable Place to Roost
An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

18. 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 cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

19. 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)
"Cute place, 70’s retro vibe was unique. Great location for exploring La Crosse. Fenced back yard worked great for our dog. Great stay."
United States
Mark S.
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
55" smart samsung curve tv with sound-bar. Hulu Live included

20. 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.
Modern Flat in Downtown La Crosse
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

Stoney Creek Hotel La Crosse - Onalaska

Stoney Creek Hotel La Crosse - Onalaska

10/10 Excellent
"Love this property. Perfect for couples families and everyone. Great location and always friendly service. Rooms are exceptional."
Dennis M 1-night trip
Posted 3 hours ago
Stoney Creek Hotel La Crosse - Onalaska

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?

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion: This holiday home rental outside of Winona offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Sugar Loaf Bluff and Mississippi River, or simply take in cultural attractions like Minnesota Marine Art Museum and Pickwick Mill. While here, Great River Bluffs State Park and Winona Mall 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.