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

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 ￥23,664
￥29,981 total
includes taxes & fees
Aug 11 - Aug 12
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, (31 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 ￥36,916
￥45,165 total
includes taxes & fees
Aug 11 - Aug 12
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 ￥32,577
￥39,768 total
includes taxes & fees
Sep 1 - Sep 2
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 ￥49,552
￥108,513 total
includes taxes & fees
Aug 16 - Aug 17
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 ￥17,038
￥21,735 total
includes taxes & fees
Aug 11 - Aug 12
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 ￥22,711
￥27,456 total
includes taxes & fees
Aug 31 - Sep 1
Big River Escape Coyote Camper #1
Terrace/patio

7. 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)
"Awesome!"
United States
Logan
The price is ￥19,736
￥25,297 total
includes taxes & fees
Aug 11 - Aug 12
The Bungaleau 1 Bedroom House In Cute Rivertown
Property grounds

8. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (41 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveler
The price is ￥14,388
￥18,509 total
includes taxes & fees
Aug 16 - Aug 17
Tamarack Point Homestead
Smart TV, books

9. 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 ￥27,403
￥41,207 total
includes taxes & fees
Aug 19 - Aug 20
Vintage Lustron Home Piece of History
Terrace/patio

10. 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 ￥18,572
￥30,344 total
includes taxes & fees
Aug 11 - Aug 12
Tiny Treehouse Cabin | Bluff Woodlands #2
Property grounds

11. 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 ￥20,275
￥32,348 total
includes taxes & fees
Aug 11 - Aug 12
Tiny Treehouse Cabin | Bluff Woodlands #3
Exterior

12. 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 ￥25,503
￥30,734 total
includes taxes & fees
Aug 12 - Aug 13
Riverfront Cabin with Private Dock
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 ￥22,711
￥27,456 total
includes taxes & fees
Sep 8 - Sep 9
Turtle Cabin Near Mississippi River
Game room

14. The Chateau on Butterfly Trail - 6 Bdrm Retreat

The Chateau on Butterfly Trail - 6 Bdrm Retreat
Fountain City
2.0 out of 10, (1 review)
"My family and I went there for the holiday weekend, we get there full of Dust, extremely dirty. Dead ladybugs in drawers, Windows sills, spider webs, refrigerator not functioning well was leaking. Was very dissapointed with the pictures vs. Reality. Do not recommend."
United States
ALFREDO M.
The price is ￥40,618
￥58,740 total
includes taxes & fees
Sep 1 - Sep 2
The Chateau on Butterfly Trail - 6 Bdrm Retreat
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 ￥30,530
￥36,870 total
includes taxes & fees
Sep 1 - Sep 2
Badger Cabin w/ Lofts, Fireplace & WiFi
Marina

16. 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 ￥24,847
￥45,066 total
includes taxes & fees
Aug 24 - Aug 25
2-bedroom house boat in beautiful La Crosse with AC comfort
Smart TV

17. 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 ￥13,883
￥29,506 total
includes taxes & fees
Aug 12 - Aug 13
Hokah Ohana House: Historic charm, Modern updates
Property grounds

18. 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)
"Cute little place. Perfect for our visit."
United States
Jeff S.
The price is ￥15,460
￥26,850 total
includes taxes & fees
Aug 21 - Aug 22
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
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 ￥21,298
￥48,442 total
includes taxes & fees
Aug 16 - Aug 17
Riverfront Twin Home
Outdoor dining

20. 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
9.0 out of 10, Wonderful, (2 reviews)
"We had a wonderful stay! The town is truly picture-perfect-charming. The property itself was clean, comfortable and thoughtfully set up, making it an easy, relax stay. Would definitely stay again and highly recommend this property. Mike the host is great!"
United States
craig h.
The price is ￥23,822
￥35,357 total
includes taxes & fees
Aug 30 - Aug 31
Mrs. Hippie Inn- Bluffside Suite near the Mississippi River in Alma, Wisconsin
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

Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

8/10 Good
"Overall, wonderful stay we had booked two rooms for three nights each besides the room is being slightly dusty, and one of our tubs didn’t drain all that well overall, I would say it was a great experience restaurant. Food is amazing. Pool area was great. Kids had a blast."
Bonnie 3-night trip
Posted 5 hours ago
Express Suites Riverport Inn & Suites

Find out more about Winona

Search for holiday rentals in Winona on Expedia! You can easily find your home rentals, villas, holiday apartments in Winona using one of the methods below:

  • View our selection of featured holiday rentals in Winona
  • Use the map to find apartments and other holiday homes in the Winona neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winona while they last

Look no further and take a look at our great range of rental properties in Winona!

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 Sugar Loaf Bluff, or simply take in cultural attractions like Minnesota Marine Art Museum and Winona County Historical Society. While here, Great River Bluffs State Park and Mississippi River 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.