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

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, (35 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 CA $241
CA $304 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $347
CA $427 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $378
CA $658 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $342
CA $422 total
includes taxes & fees
Nov 16 - Nov 17
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, (48 reviews)
"Nice quiet getaway."
United States
RICHARD
The price is CA $128
CA $164 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $175
CA $225 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $189
CA $300 total
includes taxes & fees
Oct 29 - Oct 30
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 CA $151
CA $193 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $165
CA $268 total
includes taxes & fees
Oct 26 - Oct 27
Tiny Treehouse Cabin | Bluff Woodlands #2
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 CA $180
CA $286 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $128
CA $288 total
includes taxes & fees
Oct 26 - Oct 27
Hokah Ohana House: Historic Apartment Near La Crosse, WI
A covered patio with a round table and chairs, large windows, and a view of a backyard.

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 CA $198
CA $239 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $225
CA $267 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $187
CA $227 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $474
CA $814 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $153
CA $514 total
includes taxes & fees
Oct 26 - Oct 27
Modern Downtown La Crosse Apartment
A two-story house with a covered porch, a small garden with yellow flowers, and a bird feeder.

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, (106 reviews)
"We enjoyed our stay. Thank you for the clean property and well described property."
United States
Lydia F.
The price is CA $227
CA $277 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $189
CA $433 total
includes taxes & fees
Oct 29 - Oct 30
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)
"I"
United States
Charlie
The price is CA $168
CA $285 total
includes taxes & fees
Nov 2 - Nov 3
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.
The price is CA $175
CA $543 total
includes taxes & fees
Oct 26 - Oct 27
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

Country Inn & Suites by Radisson, La Crosse, WI

Country Inn & Suites by Radisson, La Crosse, WI

10/10 Excellent
"The property was very nice! The room was well clean and stocked!"
Keannah 1-night trip
Posted 1 hour 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, 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 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona vacation rentals we have selected for you start as low as CA $225 per night. Entering your travel dates in the search wizard 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.