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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winona vacation rentals

Exterior detail

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
10.0 out of 10, Exceptional, (29 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
The price is CA $209
CA $263 total
includes taxes & fees
Sep 22 - Sep 23
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
Interior

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, (32 reviews)
"This charming home was perfect for our girls weekend. The home was very clean and offered great accommodations. We would love to stay here again!"
United States
Jenna M.
The price is CA $325
CA $398 total
includes taxes & fees
Aug 31 - Sep 1
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Terrace/patio

3. Parkside Pet Friendly Bungalow

Parkside Pet Friendly Bungalow
Winona
The price is CA $287
CA $352 total
includes taxes & fees
Aug 31 - Sep 1
Parkside Pet Friendly Bungalow
Property grounds

4. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (42 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveller
The price is CA $127
CA $163 total
includes taxes & fees
Aug 31 - Sep 1
Tamarack Point Homestead
Terrace/patio

5. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (101 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is CA $174
CA $223 total
includes taxes & fees
Aug 31 - Sep 1
The Bungaleau 1 Bedroom House In Cute Rivertown
Living area

6. Vintage Lustron Home Piece of History

Vintage Lustron Home Piece of History
Minnesota City
10.0 out of 10, Exceptional, (34 reviews)
"A beautiful comfortable welcoming home!"
United States
Jocelyn R.
The price is CA $210
CA $322 total
includes taxes & fees
Sep 1 - Sep 2
Vintage Lustron Home Piece of History
Interior

7. 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 CA $150
CA $192 total
includes taxes & fees
Aug 31 - Sep 1
Ridgetop Retreat Tiny Home, Dakota MN
Terrace/patio

8. 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 CA $164
CA $266 total
includes taxes & fees
Sep 2 - Sep 3
Tiny Treehouse Cabin | Bluff Woodlands #2
Property grounds

9. 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 $179
CA $284 total
includes taxes & fees
Aug 31 - Sep 1
Tiny Treehouse Cabin | Bluff Woodlands #3
Interior

10. Turtle Cabin Near Mississippi River

Turtle Cabin Near Mississippi River
Buffalo City
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful area, friendly locals. Perfect place to stay for aome family time! We can't wait to come back!"
United States
Sarah M.
The price is CA $172
CA $211 total
includes taxes & fees
Sep 1 - Sep 2
Turtle Cabin Near Mississippi River
Private kitchen

11. Big River Escape Coyote Camper #1

Big River Escape Coyote Camper #1
Buffalo City
10.0 out of 10, Exceptional, (1 review)
"Awesome as usual "
United States
Matthew B.
The price is CA $164
CA $202 total
includes taxes & fees
Sep 1 - Sep 2
Big River Escape Coyote Camper #1
Interior

12. 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 $213
CA $254 total
includes taxes & fees
Sep 1 - Sep 2
Badger Cabin w/ Lofts, Fireplace & WiFi
Exterior

13. 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 $212
CA $253 total
includes taxes & fees
Sep 8 - Sep 9
Riverfront Cabin with Private Dock
Living area

14. Hokah Ohana House: Historic charm, Modern updates

Hokah Ohana House: Historic charm, Modern updates
Hokah
10.0 out of 10, Exceptional, (38 reviews)
"Host very responsive, the accommodations were impeccably clean, great location and the layout was perfect for families!"
United States
Dia F.
The price is CA $122
CA $257 total
includes taxes & fees
Aug 31 - Sep 1
Hokah Ohana House: Historic charm, Modern updates
Outdoor spa tub

15. French Island w/Hot Tub, Kayak, Lake View, EV

French Island w/Hot Tub, Kayak, Lake View, EV
La Crosse
9.8 out of 10, Exceptional, (22 reviews)
"Enjoyed our stay in this peaceful, quiet neighborhood."
United States
Colleen C.
French Island w/Hot Tub, Kayak, Lake View, EV
Dining

16. 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 $289
CA $499 total
includes taxes & fees
Sep 1 - Sep 2
The Chateau on Butterfly Trail - 6 Bdrm Retreat
Property grounds

17. 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, (66 reviews)
"This place has so much personality and charm! We loved our stay, so many fun little details to enjoy. Very easily accessible to the downtown area, which made our experience very smooth. We'd love to stay there again the next time we're in La Crosse."
United States
Colin W.
The price is CA $136
CA $237 total
includes taxes & fees
Sep 23 - Sep 24
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Outdoor dining

18. Mrs. Hippie Inn- Bluffside Suite near the Mississippi River in Alma, Wisconsin

Mrs. Hippie Inn- Bluffside Suite near the Mississippi River in Alma, Wisconsin
Alma
8.6 out of 10, Excellent, (4 reviews)
"This was WAY more than we expected. Great value. Enjoyed the stay"
United States
Dana M.
The price is CA $166
CA $255 total
includes taxes & fees
Aug 31 - Sep 1
Mrs. Hippie Inn- Bluffside Suite near the Mississippi River in Alma, Wisconsin
Outdoor dining

19. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (59 reviews)
"Great property! Enjoyed the property and outdoor space was amazing! While there is not conventional central air, the space stayed cool."
United States
Melissa
The price is CA $188
CA $427 total
includes taxes & fees
Aug 31 - Sep 1
Riverfront Twin Home
Marina

20. 2-bedroom house boat in beautiful La Crosse with AC comfort

2-bedroom house boat in beautiful La Crosse with AC comfort
West La Crosse
10.0 out of 10, Exceptional, (9 reviews)
"Being our first experience lodging on a house boat, we felt as though we were staying in luxury. Unexpectedly, the boat was fully equipped with everything. The owner has it tastefully decorated, neat and very clean. Good location and within walking of a couple popular bar/restaurant eateries, although many around the city (college town). The welcome notebook inside the boat explains everything, with contact information. We fished each day off the boat using our own gear, unfortunately, not...
United States
Paula
The price is CA $219
CA $375 total
includes taxes & fees
Sep 22 - Sep 23
2-bedroom house boat in beautiful La Crosse with AC comfort
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
"Our room was updated and clean. Hotel was full but never felt crowded. Pool and pool area was clean and not overly chlorinated. Well done! Staff was great! Fitness room was a good bonus for us. Will definitely come again."
Julie 4-night trip
Posted 2 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, 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 $192 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?

The Hen House Retreat - A Comfortable Place to Roost: This vacation home rental outside of Winona is located in a rural location and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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 Lake Park and Mississippi River, or simply take in cultural attractions like Minnesota Marine Art Museum and Winona County Historical Society. While here, Great River Bluffs State Park and Altra Federal Credit Union Stadium 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.