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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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, (28 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
The price is AED 551
AED 702 total
includes taxes & fees
17 Aug - 18 Aug
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 AED 859
AED 1,059 total
includes taxes & fees
16 Aug - 17 Aug
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 AED 784
AED 971 total
includes taxes & fees
1 Sep - 2 Sep
Parkside Pet Friendly Bungalow
Property grounds

4. Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater

Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater
Winona
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful property- there were so many fun things to do and loved the location."
United States
Sean J.
The price is AED 1,154
AED 2,550 total
includes taxes & fees
20 Aug - 21 Aug
Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater
Interior

5. Ridgetop Retreat Tiny Home, Dakota MN

Ridgetop Retreat Tiny Home, Dakota MN
Dakota
9.8 out of 10, Exceptional, (9 reviews)
"Wonderful location, nice people"
United States
robert
The price is AED 397
AED 506 total
includes taxes & fees
17 Aug - 18 Aug
Ridgetop Retreat Tiny Home, Dakota MN
Coffee/tea maker, fridge, microwave, oven

6. 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 AED 598
AED 724 total
includes taxes & fees
15 Sep - 16 Sep
Big River Escape Coyote Camper #1
Property grounds

7. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (42 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveler
The price is AED 335
AED 431 total
includes taxes & fees
16 Aug - 17 Aug
Tamarack Point Homestead
Terrace/patio

8. 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 AED 459
AED 589 total
includes taxes & fees
16 Aug - 17 Aug
The Bungaleau 1 Bedroom House In Cute Rivertown
Living area

9. Farmhouse Apartment - River Road Historic Home

Farmhouse Apartment - River Road Historic Home
Fountain City
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful property with views of the Mississippi. Host checked in on us often and was very accommodating. We really enjoyed reading about the history of the home. There were so many cute details including a framed print of the original house plans. Nice place to stay."
United States
Heather O.
The price is AED 496
AED 841 total
includes taxes & fees
24 Aug - 25 Aug
Farmhouse Apartment - River Road Historic Home
Smart TV, books

10. Vintage Lustron Home Piece of History

Vintage Lustron Home Piece of History
Minnesota City
10.0 out of 10, Exceptional, (34 reviews)
"I loved staying here! The interior was comfortable, cozy, and fascinating! "
United States
melanie
The price is AED 705
AED 1,044 total
includes taxes & fees
13 Sep - 14 Sep
Vintage Lustron Home Piece of History
Terrace/patio

11. 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 AED 432
AED 714 total
includes taxes & fees
17 Aug - 18 Aug
Tiny Treehouse Cabin | Bluff Woodlands #2
Property grounds

12. 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 AED 472
AED 761 total
includes taxes & fees
16 Aug - 17 Aug
Tiny Treehouse Cabin | Bluff Woodlands #3
Interior

13. 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 AED 455
AED 558 total
includes taxes & fees
23 Aug - 24 Aug
Turtle Cabin Near Mississippi River
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 AED 477
AED 580 total
includes taxes & fees
31 Aug - 1 Sep
Riverfront Cabin with Private Dock
Interior

15. 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 AED 563
AED 680 total
includes taxes & fees
1 Sep - 2 Sep
Badger Cabin w/ Lofts, Fireplace & WiFi
Property grounds

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, (65 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 AED 360
AED 625 total
includes taxes & fees
21 Aug - 22 Aug
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Marina

17. 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, (7 reviews)
The price is AED 578
AED 1,057 total
includes taxes & fees
24 Aug - 25 Aug
2-bedroom house boat in beautiful La Crosse with AC comfort
Smart TV

18. 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 AED 323
AED 687 total
includes taxes & fees
31 Aug - 1 Sep
Hokah Ohana House: Historic charm, Modern updates
Outdoor dining

19. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (56 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 AED 496
AED 1,136 total
includes taxes & fees
16 Aug - 17 Aug
Riverfront Twin Home
Private kitchen

20. Warm and Cozy Upstairs Apartment

Warm and Cozy Upstairs Apartment
Caledonia
9.4 out of 10, Exceptional, (15 reviews)
"So cozy and nice "
United States
Heidi P.
The price is AED 413
AED 599 total
includes taxes & fees
19 Aug - 20 Aug
Warm and Cozy Upstairs Apartment
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
"It was very clean and a decent price!!"
Todd 1-night trip
Posted 2 hours ago
Gundersen Hotel & Suites

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 Lake Lodge Recreation Center 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.