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

Our top choices for Winona vacation rentals

Exterior detail

Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO
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.
$171 nightly
The price is $190
Aug 5 - Aug 6
Total with taxes and fees
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO
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)
"Beautiful home we had a wonderful stay!!!"
United States
Thomas L.
$264 nightly
The price is $284
Aug 2 - Aug 3
Total with taxes and fees
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.
$639 nightly
The price is $688
Aug 2 - Aug 3
Total with taxes and fees
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
$128 nightly
The price is $138
Jul 30 - Jul 31
Total with taxes and fees
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)
$246 nightly
The price is $272
Aug 4 - Aug 5
Total with taxes and fees
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.
$138 nightly
The price is $146
Aug 4 - Aug 5
Total with taxes and fees
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
$145 nightly
The price is $160
Jul 30 - Jul 31
Total with taxes and fees
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 traveler
$111 nightly
The price is $117
Aug 10 - Aug 11
Total with taxes and fees
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.
$172 nightly
The price is $185
Aug 7 - Aug 8
Total with taxes and fees
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.
$216 nightly
The price is $228
Aug 4 - Aug 5
Total with taxes and fees
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
$225 nightly
The price is $242
Aug 3 - Aug 4
Total with taxes and fees
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.
$191 nightly
The price is $205
Jul 30 - Jul 31
Total with taxes and fees
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.
$141 nightly
The price is $162
Aug 21 - Aug 22
Total with taxes and fees
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.
$159 nightly
The price is $168
Aug 4 - Aug 5
Total with taxes and fees
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.
$153 nightly
The price is $162
Aug 4 - Aug 5
Total with taxes and fees
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
$268 nightly
The price is $308
Aug 3 - Aug 4
Total with taxes and fees
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.
$153 nightly
The price is $163
Jul 30 - Jul 31
Total with taxes and fees
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.
$337 nightly
The price is $388
Aug 2 - Aug 3
Total with taxes and fees
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.
$378 nightly
The price is $435
Aug 3 - Aug 4
Total with taxes and fees
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.
$175 nightly
The price is $187
Aug 5 - Aug 6
Total with taxes and fees
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

Pearl Street Hotel & Suites

Pearl Street Hotel & Suites

10/10 Excellent
"I checked in VERY late at 2:30 AM and that went well. The parking for me was in the huge parking strucure nex door and that went well. The interior of this property looks a little tired. A quick paint touchup here and there wouls be great. My unit was on the fifth floor and was pretty quiet and the bedding was fresh and conducive for sleep. Checkout was quick and positive."
GREG 2-night trip
Posted less than an hour ago
Pearl Street Hotel & Suites

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Winona in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $117 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion: This vacation home rental outside of Winona offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Winona?

Expedia has 12 vacation 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 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.