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

Winona Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winona vacation 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.
$194 nightly
The price is $216
Nov 23 - Nov 24
Total with taxes and fees
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.
$276 nightly
The price is $297
Nov 4 - Nov 5
Total with taxes and fees
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.
$398 nightly
The price is $442
Nov 8 - Nov 9
Total with taxes and fees
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.
$235 nightly
The price is $260
Nov 2 - Nov 3
Total with taxes and fees
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
$112 nightly
The price is $118
Nov 1 - Nov 2
Total with taxes and fees
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.
$145 nightly
The price is $160
Nov 5 - Nov 6
Total with taxes and fees
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.
$178 nightly
The price is $191
Oct 31 - Nov 1
Total with taxes and fees
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.
$215 nightly
The price is $231
Nov 16 - Nov 17
Total with taxes and fees
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.
$184 nightly
The price is $198
Nov 7 - Nov 8
Total with taxes and fees
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.
$156 nightly
The price is $164
Nov 2 - Nov 3
Total with taxes and fees
Cozy River Cabin w/ Loft & Screened Porch
A calm lake with docks, grassy banks, and a clear sky.

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.
$142 nightly
The price is $150
Nov 30 - Dec 1
Total with taxes and fees
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.
$182 nightly
The price is $195
Nov 1 - Nov 2
Total with taxes and fees
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.
$208 nightly
The price is $220
Oct 31 - Nov 1
Total with taxes and fees
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.
$265 nightly
The price is $305
Nov 1 - Nov 2
Total with taxes and fees
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.
$497 nightly
The price is $526
Nov 1 - Nov 2
Total with taxes and fees
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
$167 nightly
The price is $192
Nov 2 - Nov 3
Total with taxes and fees
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.
$303 nightly
The price is $348
Nov 1 - Nov 2
Total with taxes and fees
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.
$185 nightly
The price is $199
Nov 1 - Nov 2
Total with taxes and fees
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
$155 nightly
The price is $164
Nov 12 - Nov 13
Total with taxes and fees
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.
$285 nightly
The price is $305
Nov 1 - Nov 2
Total with taxes and fees
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

Country Inn & Suites by Radisson, La Crosse, WI

Country Inn & Suites by Radisson, La Crosse, WI

10/10 Excellent
"Staff is very nice. Hotel location is convenient right next to the highway."
Michelle 1-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, La Crosse, WI

Find out more about Winona

Everything you need to know about Winona vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winona vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winona vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winona in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $160 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winona?

Yes, there are vacation rentals in Winona near Valencia Arts Center, or you can choose a secluded option if you want 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 vacation rentals that Winona has to offer?

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion: This vacation 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 you can cook with friends or family.

How many vacation rentals are there in Winona?

Expedia has 13 vacation 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 vacation rentals like in Winona?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Winona. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.