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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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, (29 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
$171 nightly
The price is $190
Sep 22 - Sep 23
Total with taxes and fees
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, (33 reviews)
"A charming place to stay with a spacious primary bedroom, laundry room, and living areas. The backyard patio is a perfect place for a morning coffee and a quiet evening. We would definitely rebook on our next visit."
United States
Mainul
$264 nightly
The price is $284
Sep 13 - Sep 14
Total with taxes and fees
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Terrace/patio

3. Parkside Pet Friendly Bungalow

Parkside Pet Friendly Bungalow
Winona
$228 nightly
The price is $252
Sep 13 - Sep 14
Total with taxes and fees
Parkside Pet Friendly Bungalow
Outdoor dining

4. Charming Brick Farmhouse with a Touch of Elegance. -Winona

Charming Brick Farmhouse with a Touch of Elegance. -Winona
Winona
10.0 out of 10, Exceptional, (147 reviews)
"Absolutely amazing! So much charm and space…could definitely stay here again!"
United States
Lynn B.
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Terrace/patio

5. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (103 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
$145 nightly
The price is $160
Sep 13 - Sep 14
Total with taxes and fees
The Bungaleau 1 Bedroom House In Cute Rivertown
Living area

6. Vintage Lustron Home Piece of History

Vintage Lustron Home Piece of History
Minnesota City
10.0 out of 10, Exceptional, (35 reviews)
"A beautiful comfortable welcoming home!"
United States
Jocelyn R.
$213 nightly
The price is $229
Sep 21 - Sep 22
Total with taxes and fees
Vintage Lustron Home Piece of History
Property grounds

7. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (45 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveler
$111 nightly
The price is $117
Sep 13 - Sep 14
Total with taxes and fees
Tamarack Point Homestead
Terrace/patio

8. 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.
$179 nightly
The price is $192
Sep 11 - Sep 12
Total with taxes and fees
Tiny Treehouse Cabin | Bluff Woodlands #2
Interior

9. Ridgetop Retreat Tiny Home, Dakota MN

Ridgetop Retreat Tiny Home, Dakota MN
Dakota
9.4 out of 10, Exceptional, (10 reviews)
"Everything was perfect for our one night stay… owner was very helpful and easy to reach. Only small issue was that it was a little difficult to get up and down the ladders to the lofted beds.. but now that we know what to expect, we would definitely consider staying here again!"
United States
Jessica W.
$128 nightly
The price is $138
Sep 16 - Sep 17
Total with taxes and fees
Ridgetop Retreat Tiny Home, Dakota MN
Private kitchen

10. 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
Sep 13 - Sep 14
Total with taxes and fees
Big River Escape Coyote Camper #1
Exterior

11. 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.
$159 nightly
The price is $168
Sep 15 - Sep 16
Total with taxes and fees
Riverfront Cabin with Private Dock
Interior

12. 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
Oct 1 - Oct 2
Total with taxes and fees
Turtle Cabin Near Mississippi River
Terrace/patio

13. Tiny Treehouse Cabin | Bluff Woodlands #1

Tiny Treehouse Cabin | Bluff Woodlands #1
Elba
9.6 out of 10, Exceptional, (9 reviews)
"Great area a place to stay. "
United States
Paul T.
$191 nightly
The price is $205
Sep 13 - Sep 14
Total with taxes and fees
Tiny Treehouse Cabin | Bluff Woodlands #1
Interior

14. 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.
$175 nightly
The price is $185
Sep 13 - Sep 14
Total with taxes and fees
Badger Cabin w/ Lofts, Fireplace & WiFi
Outdoor dining

15. 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
8.6 out of 10, Excellent, (4 reviews)
"This was WAY more than we expected. Great value. Enjoyed the stay"
United States
Dana M.
$192 nightly
The price is $214
Sep 20 - Sep 21
Total with taxes and fees
Mrs. Hippie Inn- Bluffside Suite near the Mississippi River in Alma, Wisconsin
Dining

16. The Chateau on Butterfly Trail - 6 Bdrm Retreat

The Chateau on Butterfly Trail - 6 Bdrm Retreat
Fountain City
7.4 out of 10, Good, (3 reviews)
"Thankyou"
United States
Kathy P.
$384 nightly
The price is $406
Sep 14 - Sep 15
Total with taxes and fees
The Chateau on Butterfly Trail - 6 Bdrm Retreat
Outdoor dining

17. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (61 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
$265 nightly
The price is $305
Sep 13 - Sep 14
Total with taxes and fees
Riverfront Twin Home
Outdoor spa tub

18. French Island w/Hot Tub, Kayak, Lake View, EV

French Island w/Hot Tub, Kayak, Lake View, EV
La Crosse
9.8 out of 10, Exceptional, (22 reviews)
"Enjoyed our stay in this peaceful, quiet neighborhood."
United States
Colleen C.
French Island w/Hot Tub, Kayak, Lake View, EV
Living area

19. Hokah Ohana House: Historic charm, Modern updates

Hokah Ohana House: Historic charm, Modern updates
Hokah
10.0 out of 10, Exceptional, (39 reviews)
"Host very responsive, the accommodations were impeccably clean, great location and the layout was perfect for families!"
United States
Dia F.
$169 nightly
The price is $180
Sep 13 - Sep 14
Total with taxes and fees
Hokah Ohana House: Historic charm, Modern updates
Living area

20. Great River Road - Victorian Historic Home (1898)

Great River Road - Victorian Historic Home (1898)
Fountain City
9.4 out of 10, Exceptional, (11 reviews)
"We had an amazing 3 nights here. It’s a beautiful, cozy house with so much room for cooking and visiting family !"
United States
amy r.
$686 nightly
The price is $724
Sep 14 - Sep 15
Total with taxes and fees
Great River Road - Victorian Historic Home (1898)
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

Radisson Hotel La Crosse

Radisson Hotel La Crosse

8/10 Good
".."
Joel 2-night trip
Posted 1 hour ago
Radisson Hotel La Crosse

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 $138 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?

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.