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

Winona Holiday Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Winona holiday rentals

Exterior detail

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, (27 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
The price is HK$1,176
HK$1,490 total
includes taxes & fees
5 Aug - 6 Aug
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
Interior

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, (30 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 HK$1,835
HK$2,228 total
includes taxes & fees
2 Aug - 3 Aug
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Property grounds

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 HK$2,463
HK$5,393 total
includes taxes & fees
2 Aug - 3 Aug
Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater
Interior

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 HK$847
HK$1,080 total
includes taxes & fees
11 Aug - 12 Aug
Ridgetop Retreat Tiny Home, Dakota MN
Marina

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, (6 reviews)
The price is HK$1,193
HK$2,176 total
includes taxes & fees
2 Aug - 3 Aug
2-bedroom house boat in beautiful La Crosse with AC comfort
Coffee/tea maker, fridge, microwave, oven

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 HK$925
HK$1,142 total
includes taxes & fees
4 Aug - 5 Aug
Big River Escape Coyote Camper #1
Terrace/patio

The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (100 reviews)
"Awesome!"
United States
Logan
The price is HK$981
HK$1,257 total
includes taxes & fees
2 Aug - 3 Aug
The Bungaleau 1 Bedroom House In Cute Rivertown
Property grounds

Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (40 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveller
The price is HK$715
HK$920 total
includes taxes & fees
10 Aug - 11 Aug
Tamarack Point Homestead
Terrace/patio

Treehouse Cabin in the Bluff Woodlands

Treehouse Cabin in the Bluff Woodlands
Elba
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful area enjoyed our stay immensely"
United Kingdom
I.M l.
The price is HK$881
HK$1,454 total
includes taxes & fees
7 Aug - 8 Aug
Treehouse Cabin in the Bluff Woodlands
Living area

Farmhouse Apartment - River Road Historic Home

Farmhouse Apartment - River Road Historic Home
Fountain City
10.0 out of 10, Exceptional, (23 reviews)
"We enjoyed watching the river. We especially liked watching the migrating birds and the tug boats. The property was clean and the owner was responsive when we had a question. Check out was easy and the only cleaning requirements were to wash any dishes and clean up any messes."
United States
Linda S.
The price is HK$1,059
HK$1,787 total
includes taxes & fees
4 Aug - 5 Aug
Farmhouse Apartment - River Road Historic Home
Smart TV, books

Vintage Lustron Home Piece of History

Vintage Lustron Home Piece of History
Minnesota City
10.0 out of 10, Exceptional, (33 reviews)
"I loved staying here! The interior was comfortable, cozy, and fascinating! "
United States
melanie
The price is HK$1,249
HK$1,901 total
includes taxes & fees
3 Aug - 4 Aug
Vintage Lustron Home Piece of History
Property grounds

Treehouse Cabin in the Bluff Woodlands South

Treehouse Cabin in the Bluff Woodlands South
Elba
10.0 out of 10, Exceptional, (13 reviews)
"My family of 4 had a wonderful stay!"
United States
Josh S.
The price is HK$1,008
HK$1,608 total
includes taxes & fees
2 Aug - 3 Aug
Treehouse Cabin in the Bluff Woodlands South
Property grounds

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 HK$768
HK$1,335 total
includes taxes & fees
21 Aug - 22 Aug
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Exterior

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 HK$1,083
HK$1,307 total
includes taxes & fees
4 Aug - 5 Aug
Turtle Cabin Near Mississippi River
Exterior

Riverfront Cabin with Private Dock

Riverfront Cabin with Private Dock
Buffalo City
10.0 out of 10, Exceptional, (4 reviews)
"Great place!!!"
United States
Cynthia B.
The price is HK$1,018
HK$1,239 total
includes taxes & fees
4 Aug - 5 Aug
Riverfront Cabin with Private Dock
Outdoor dining

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 HK$1,059
HK$2,417 total
includes taxes & fees
3 Aug - 4 Aug
Riverfront Twin Home
Private kitchen

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 HK$882
HK$1,278 total
includes taxes & fees
1 Aug - 2 Aug
Warm and Cozy Upstairs Apartment
Coffee/tea maker, fridge, microwave, oven

Modern Downtown La Crosse Apartment

Modern Downtown La Crosse Apartment
Historic Downtown La Crosse
9.4 out of 10, Exceptional, (73 reviews)
"Communication with the host was great…..location is amazing if you want to be close to everything! "
United States
Lisa C.
The price is HK$980
HK$3,039 total
includes taxes & fees
2 Aug - 3 Aug
Modern Downtown La Crosse Apartment
Interior

Warm Season Haven | Scenic Bluffs

Warm Season Haven | Scenic Bluffs
Holy Trinity-Longfellow
9.4 out of 10, Exceptional, (39 reviews)
"Lovely atmosphere- great location. It was perfect for our family getaway to visit our son in college."
United States
Lynn M.
The price is HK$1,177
HK$3,564 total
includes taxes & fees
3 Aug - 4 Aug
Warm Season Haven | Scenic Bluffs
Smart TV

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 HK$690
HK$1,467 total
includes taxes & fees
5 Aug - 6 Aug
Hokah Ohana House: Historic charm, Modern updates
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

Stoney Creek Hotel La Crosse - Onalaska

Stoney Creek Hotel La Crosse - Onalaska

10/10 Excellent
"Upon arrival, check in was very pleasant and efficient. Room was clean, spacious and the king bed was comfortable. The staff was great at registration, Lumber Jack’s saloon and throughout the hotel. The pool (indoor with swim out to outdoor) and hot tub were both very nice. The outdoor lounge area for the pool and Lumber Jack’s were both nice. The breakfast was very good in a well presented and clean environment."
Kandyce L 1-night trip
Posted 3 hours ago
Stoney Creek Hotel La Crosse - Onalaska

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 holiday rentals in Winona?

Yes, there are holiday rentals in Winona close to Valencia Arts Center, or you can select a more secluded option if you're looking for 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 holiday rentals that Winona has to offer?

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

How many holiday rentals are there in Winona?

Expedia has 13 holiday rentals for your stay in Winona.

What can I see and do in Winona?

Enjoy the outdoors at Lake Lodge Recreation Center and Lake Park, or simply take in cultural attractions like Winona County Historical Society and Minnesota Marine Art Museum. While here, Sugar Loaf Bluff and Great River Bluffs State Park are other places worth a visit.

What are holiday rentals like in Winona?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winona. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for families.