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

Winona Vacation Rentals

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Our top choices for Winona vacation rentals

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.
The price is CA $207
CA $260 total
includes taxes & fees
Sep 22 - Sep 23
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons

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
The price is CA $323
CA $398 total
includes taxes & fees
Sep 13 - Sep 14
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona

3. Parkside Pet Friendly Bungalow

Parkside Pet Friendly Bungalow
Winona
The price is CA $290
CA $357 total
includes taxes & fees
Sep 20 - Sep 21
Parkside Pet Friendly Bungalow

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.
The price is CA $440
CA $734 total
includes taxes & fees
Sep 17 - Sep 18
Charming Brick Farmhouse with a Touch of Elegance. -Winona

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.
The price is CA $172
CA $221 total
includes taxes & fees
Sep 10 - Sep 11
The Bungaleau 1 Bedroom House In Cute Rivertown

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.
The price is CA $205
CA $318 total
includes taxes & fees
Sep 21 - Sep 22
Vintage Lustron Home Piece of History

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 traveller
The price is CA $126
CA $162 total
includes taxes & fees
Sep 13 - Sep 14
Tamarack Point Homestead

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.
The price is CA $162
CA $264 total
includes taxes & fees
Sep 10 - Sep 11
Tiny Treehouse Cabin | Bluff Woodlands #2

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.
The price is CA $149
CA $190 total
includes taxes & fees
Sep 10 - Sep 11
Ridgetop Retreat Tiny Home, Dakota MN

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.
The price is CA $163
CA $201 total
includes taxes & fees
Sep 14 - Sep 15
Big River Escape Coyote Camper #1

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.
The price is CA $181
CA $220 total
includes taxes & fees
Sep 15 - Sep 16
Riverfront Cabin with Private Dock

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.
The price is CA $183
CA $222 total
includes taxes & fees
Sep 10 - Sep 11
Turtle Cabin Near Mississippi River

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.
The price is CA $177
CA $281 total
includes taxes & fees
Sep 10 - Sep 11
Tiny Treehouse Cabin | Bluff Woodlands #1

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.
The price is CA $211
CA $252 total
includes taxes & fees
Sep 13 - Sep 14
Badger Cabin w/ Lofts, Fireplace & WiFi

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.
The price is CA $197
CA $292 total
includes taxes & fees
Sep 10 - Sep 11
Mrs. Hippie Inn- Bluffside Suite near the Mississippi River in Alma, Wisconsin

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.
The price is CA $346
CA $569 total
includes taxes & fees
Sep 10 - Sep 11
The Chateau on Butterfly Trail - 6 Bdrm Retreat

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
The price is CA $186
CA $422 total
includes taxes & fees
Sep 10 - Sep 11
Riverfront Twin Home

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.
The price is CA $179
CA $434 total
includes taxes & fees
Sep 15 - Sep 16
French Island w/Hot Tub, Kayak, Lake View, EV

19. 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 CA $115
CA $248 total
includes taxes & fees
Sep 13 - Sep 14
Hokah Ohana House: Historic charm, Modern updates

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.
The price is CA $620
CA $998 total
includes taxes & fees
Sep 14 - Sep 15
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

Find out more about Winona

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winona. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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.