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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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 AU$296
includes taxes & fees
23 Nov - 24 Nov
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 AU$409
includes taxes & fees
4 Nov - 5 Nov
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, (153 reviews)
"This was a fabulous place to stay- clean, comfortable, beautiful and accessible."
United States
Ruth S.
The price is AU$588
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 AU$350
includes taxes & fees
1 Nov - 2 Nov
Parkside Pet Friendly Bungalow
A rural landscape with a barn, a small house, and a large house with a porch.

5. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (49 reviews)
"Nice quiet getaway."
United States
RICHARD
The price is AU$169
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, (108 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is AU$217
includes taxes & fees
5 Nov - 6 Nov
The Bungaleau 1 Bedroom House In Cute Rivertown
A wooden cabin with a porch, a door, and a small seating area with two chairs.

7. 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$263
includes taxes & fees
3 Nov - 4 Nov
Tiny Treehouse Cabin | Bluff Woodlands #2
A living room with a television, sofa, coffee table, and shelves with decorative items.

8. 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$333
includes taxes & fees
16 Nov - 17 Nov
Vintage Lustron Home Piece of History
A cabin surrounded by dense forest, with a wooden deck and a hammock.

9. 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$283
includes taxes & fees
10 Nov - 11 Nov
Tiny Treehouse Cabin | Bluff Woodlands #1
A rustic wooden pavilion with picnic tables, surrounded by a gravel area and grassy lawn.

10. Cozy River Cabin w/ Loft & Screened Porch

Cozy River Cabin w/ Loft & Screened Porch
Buffalo City
10.0 out of 10, Exceptional, (2 reviews)
"It was a in and out stay. Would have liked to been able to check in earlier since we came from a distance and woulda been nice to have a place to change church clothes without a fee. Other than that all worked out."
United States
John S.
The price is AU$223
includes taxes & fees
1 Dec - 2 Dec
Cozy River Cabin w/ Loft & Screened Porch
Exterior

11. 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 AU$214
includes taxes & fees
1 Nov - 2 Nov
Riverfront Cabin with Private Dock
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.

12. Hokah Ohana House| 2BR Near La Crosse WI

Hokah Ohana House| 2BR Near La Crosse WI
Hokah
10.0 out of 10, Exceptional, (41 reviews)
"Very comfortable and had everything you need to feel at home!"
United States
David R.
The price is AU$280
includes taxes & fees
1 Nov - 2 Nov
Hokah Ohana House| 2BR Near La Crosse WI
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 AU$250
includes taxes & fees
1 Dec - 2 Dec
Badger Cabin w/ Lofts, Fireplace & WiFi
An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

14. 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 AU$411
includes taxes & fees
1 Nov - 2 Nov
Riverfront Twin Home
A spacious living room with a stone fireplace, leather furniture, and a large window providing natural light.

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 AU$682
includes taxes & fees
2 Nov - 3 Nov
The Chateau on Butterfly Trail - 6 Bdrm Retreat
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

16. 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, (71 reviews)
"Liked the retro decor, outdoor gazebo, firepit and location."
United States
Tim
The price is AU$263
includes taxes & fees
2 Nov - 3 Nov
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
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 AU$487
includes taxes & fees
1 Nov - 2 Nov
Modern Downtown La Crosse Apartment
A two-story house with a covered porch, a small garden with yellow flowers, and a bird feeder.

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

The Hen House Retreat - A Comfortable Place to Roost
Highland
9.6 out of 10, Exceptional, (109 reviews)
"We enjoyed our stay. Thank you for the clean property and well described property."
United States
Lydia F.
The price is AU$269
includes taxes & fees
1 Nov - 2 Nov
The Hen House Retreat - A Comfortable Place to Roost
A living room with a fireplace, a sofa, a wooden coffee table, and a patterned rug.

19. Stylish 1 bedroom cottage along the Mississippi River

Stylish 1 bedroom cottage along the Mississippi River
Stoddard
9.6 out of 10, Exceptional, (38 reviews)
"Very nice and clean property. Private location."
United States
Kevin
The price is AU$236
includes taxes & fees
12 Nov - 13 Nov
Stylish 1 bedroom cottage along the Mississippi River
A bedroom with a bed, bedside table, lamp, and a view of the adjacent room through a wooden-framed door.

20. 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, (36 reviews)
"The loft apartment above the International Owl Center was beautiful, spacious, well furnished and very comfortable.Just 3 blocks from the start point of the Root River bike trail, and a short scenic drive away from a variety of outdoor recreation activities and dining options. We had a lovely weekend stay, and were very well supported by the owner. I highly recommend this place for a relaxing or invigorating stay!"
United States
Richard C.
The price is AU$405
includes taxes & fees
1 Nov - 2 Nov
Spacious 2-bedroom loft above the International Owl Center in Houston, MN
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

Gundersen Hotel & Suites

Gundersen Hotel & Suites

10/10 Excellent
"Nice place to stay. Clean and very well kept."
Ryan 2-night trip
Posted 2 hours ago
Gundersen Hotel & Suites

Find out more about Winona

Everything you need to know about Winona 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 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winona holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona. 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 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 holiday rentals we have selected for you start as low as AU$217 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.