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Winona Holiday Rentals

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Our top choices for Winona holiday rentals

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a wonderful time and would defiinitely stay again. "
United States
Julie
The price is NZ$394
includes taxes & fees
30 Dec - 31 Dec
Big River Escape Parkside Bungalow
10.0 out of 10, Exceptional, (20)
"Had everything we needed and great communication for our weekend stay. "
United States
Tanya G.
The price is NZ$315
includes taxes & fees
30 Dec - 31 Dec
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO
10.0 out of 10, Exceptional, (25)
"Beautiful home we had a wonderful stay!!!"
United States
Thomas L.
The price is NZ$548
includes taxes & fees
2 Jan - 3 Jan 2026
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
10.0 out of 10, Exceptional, (138)
"Beautiful home! Close to SMU campus. "
United States
Lucy M.
The price is NZ$743
includes taxes & fees
5 Jan - 6 Jan 2026
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Farm Stay, convenient yet quiet - complete with cows in the backyard!
3.0 star property
9.2 out of 10, Wonderful, (40)
"Place was clean and comfortable. "
United States
Tristan
The price is NZ$202
includes taxes & fees
27 Jan - 28 Jan 2026
Big River Escape Riverside Cabins
9.8 out of 10, Exceptional, (15)
"Beautiful area enjoyed our stay immensely"
United Kingdom
I.M l.
The price is NZ$236
includes taxes & fees
12 Jan - 13 Jan 2026
Treehouse Cabin in the Bluff Woodlands

Holiday Home in Arcadia

Tamarack Point Homestead
10.0 out of 10, Exceptional, (32)
"Cozy place, had everything we needed, it was quiet and peaceful! Highly recommend."
United States
Luke H.
The price is NZ$201
includes taxes & fees
30 Dec - 31 Dec
Tamarack Point Homestead
9.6 out of 10, Exceptional, (9)
"Great relaxing place! "
United States
James H.
The price is NZ$294
includes taxes & fees
30 Dec - 31 Dec
Treehouse Cabin in the Bluff Woodlands North

Apartment in Caledonia

Warm and Cozy Upstairs Apartment
9.4 out of 10, Exceptional, (14)
"Very comfortable and in an excellent location. Space was comfortable and very quiet "
United States
Sue G.
Warm and Cozy Upstairs Apartment

Apartment in Holy Trinity-Longfellow

Hidden Gem - 1BR/1Bath in Lax WI
9.6 out of 10, Exceptional, (15)
"A lovely, spacious, clean apartment above a yummy restaurant in a quiet residential neighborhood. We stayed there when we were in town for a 6-hour race in Goose Island State Park, and it was perfect! "
United States
Amy
Hidden Gem - 1BR/1Bath in Lax WI
10.0 out of 10, Exceptional, (32)
"Perfect place for 4 of us to stay while visiting for a wedding. "
United States
Jeff W.
The price is NZ$319
includes taxes & fees
4 Jan - 5 Jan 2026
Hokah Ohana House: Historic charm, Modern updates
10.0 out of 10, Exceptional, (2)
"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 NZ$229
includes taxes & fees
30 Dec - 31 Dec
Great River Road Cabin on the Mississippi Backwaters Turtle Cabin
9.8 out of 10, Exceptional, (46)
"Wonderful stay, super cozy, perfect for a getaway "
United States
Katie C.
The price is NZ$262
includes taxes & fees
1 Jan - 2 Jan 2026
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
2-bedroom apartment over storefront in pleasant down town Ettrick

Holiday Home in La Crosse

Riverfront Twin Home
10.0 out of 10, Exceptional, (44)
"Great place to stay! Had everything we needed!"
United States
Angie C.
The price is NZ$528
includes taxes & fees
30 Dec - 31 Dec
Riverfront Twin Home

Holiday Home in Minnesota City

Vintage Lustron Home Piece of History
10.0 out of 10, Exceptional, (28)
"I loved staying here! The interior was comfortable, cozy, and fascinating! "
United States
melanie
The price is NZ$363
includes taxes & fees
6 Jan - 7 Jan 2026
Vintage Lustron Home Piece of History

Apartment in Historic Downtown La Crosse

Downtown La Crosse Modern Flat
9.4 out of 10, Exceptional, (63)
"The place is right in the middle of shops, restaurants, and just a short walk from the river and park"
United States
Adam C.
The price is NZ$556
includes taxes & fees
4 Jan - 5 Jan 2026
Downtown La Crosse Modern Flat
9.8 out of 10, Exceptional, (87)
"Very nice perfect for us, would rent again!"
United States
Mitchell G.
The price is NZ$340
includes taxes & fees
5 Jan - 6 Jan 2026
The Hen House Retreat - A Comfortable Place to Roost

Holiday Home in Powell-Poage-Hamilton

Jake's Place
9.8 out of 10, Exceptional, (8)
"Great place, great location. Very clean & practical! "
United States
Cori C.
The price is NZ$564
includes taxes & fees
28 Jan - 29 Jan 2026
Jake's Place
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

Find out more about Winona

Everything you need to know about Winona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winona holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona holiday rentals we have selected for you start as low as NZ$202 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 holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Winona?

Yes, there are holiday rentals close to the most popular sights in Winona, 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?

Spacious house w/hot tub & river view: This highly rated holiday home rental in Winona is located on a river, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, in addition to a kitchen with a stovetop and a microwave. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub. Our travellers also rate Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater as a favourite home for rent in Winona.

How many holiday rentals are there in Winona?

Expedia has 14 holiday rentals for your stay in Winona.

What can I see and do in Winona?

Enjoy the outdoors at Lake Lodge Recreation Center 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 Aghaming Park And Preserve 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.