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

Winona Vacation Rentals

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    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Winona vacation rentals

A modern apartment with a staircase, a dining area, and a living space.

1. 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
$268 nightly
The price is $288
Sep 1 - Sep 2
Total with taxes and fees
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
A two-story house with a wooden staircase leading to a yellow door, a brick wall, and a window with a white frame.

2. 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.
$172 nightly
The price is $191
Sep 22 - Sep 23
Total with taxes and fees
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
A patio with two chairs and a table, a fire pit, a wooden fence, and a shed in the background.

3. Parkside Pet Friendly Bungalow

Parkside Pet Friendly Bungalow
Winona
$235 nightly
The price is $261
Sep 20 - Sep 21
Total with taxes and fees
Parkside Pet Friendly Bungalow
A living room with a television, sofa, coffee table, and shelves with decorative items.

4. Vintage Lustron Home Piece of History

Vintage Lustron Home Piece of History
Minnesota City
10.0 out of 10, Exceptional, (34 reviews)
"A beautiful comfortable welcoming home!"
United States
Jocelyn R.
$219 nightly
The price is $236
Sep 1 - Sep 2
Total with taxes and fees
Vintage Lustron Home Piece of History
A wooden deck with a bench, a white door, and hanging flower baskets.

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, (102 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
$145 nightly
The price is $160
Sep 1 - Sep 2
Total with taxes and fees
The Bungaleau 1 Bedroom House In Cute Rivertown
A field of lavender with a path leading through it.

6. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (43 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveler
$111 nightly
The price is $117
Sep 1 - Sep 2
Total with taxes and fees
Tamarack Point Homestead
A bedroom with a bed, bedside table, lamp, and a view of the adjacent room through a wooden-framed door.

7. Spacious 2-bedroom loft above the International Owl Center in Houston, MN

Spacious 2-bedroom loft above the International Owl Center in Houston, MN
Houston
10.0 out of 10, Exceptional, (29 reviews)
"Host was very attentive and available if needed but everything was perfect. The woodwork is amazing and grand piano sounded like you were in a concert hall. We absolutely loved our stay and hope to make it back since it is such a beautiful area."
United States
Nikki W.
$285 nightly
The price is $305
Sep 2 - Sep 3
Total with taxes and fees
Spacious 2-bedroom loft above the International Owl Center in Houston, MN
A dining area with a wooden table and chairs, a kitchen with white cabinets, and two paintings on the wall.

8. 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.
$339 nightly
The price is $359
Sep 1 - Sep 2
Total with taxes and fees
The Chateau on Butterfly Trail - 6 Bdrm Retreat
A bunk bed room with a window view, a ceiling fan, and a TV.

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 1 - Sep 2
Total with taxes and fees
Ridgetop Retreat Tiny Home, Dakota MN
A wooden cabin with a porch, two chairs, and a door.

10. 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.
$181 nightly
The price is $195
Sep 2 - Sep 3
Total with taxes and fees
Tiny Treehouse Cabin | Bluff Woodlands #2
A two-story house with a covered patio, a grill, and a well-maintained lawn.

11. NEW Mississippi Riverfront Sunset House - family, friends & river come together

NEW Mississippi Riverfront Sunset House - family, friends & river come together
Buffalo City
10.0 out of 10, Exceptional, (5 reviews)
"great experience !!"
United States
pamela m.
$771 nightly
The price is $813
Sep 29 - Sep 30
Total with taxes and fees
NEW Mississippi Riverfront Sunset House - family, friends & river come together
A rustic wooden pavilion with picnic tables, surrounded by a gravel area and grassy lawn.

12. Cozy River Cabin w/ Loft & Screened Porch

Cozy River Cabin w/ Loft & Screened Porch
Buffalo City
10.0 out of 10, Exceptional, (2 reviews)
"It was a in and out stay. Would have liked to been able to check in earlier since we came from a distance and woulda been nice to have a place to change church clothes without a fee. Other than that all worked out."
United States
John S.
$156 nightly
The price is $164
Sep 1 - Sep 2
Total with taxes and fees
Cozy River Cabin w/ Loft & Screened Porch
A wooden cabin interior with a dining table, chairs, a refrigerator, a stove, and a ladder leading to a loft.

13. 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 1 - Sep 2
Total with taxes and fees
Badger Cabin w/ Lofts, Fireplace & WiFi
A living room with a fireplace, sofas, a TV, and a view of a lake.

14. Riverview, 5BR, Hot tub, Fireplace, Arcade Game

Riverview, 5BR, Hot tub, Fireplace, Arcade Game
Minneiska
$395 nightly
The price is $424
Sep 1 - Sep 2
Total with taxes and fees
Riverview, 5BR, Hot tub, Fireplace, Arcade Game
A covered deck with outdoor seating, surrounded by a forested area.

15. Tiny Treehouse Cabin | Bluff Woodlands #3

Tiny Treehouse Cabin | Bluff Woodlands #3
Elba
10.0 out of 10, Exceptional, (13 reviews)
"My family of 4 had a wonderful stay!"
United States
Josh S.
$193 nightly
The price is $207
Sep 1 - Sep 2
Total with taxes and fees
Tiny Treehouse Cabin | Bluff Woodlands #3

16. 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.
$171 nightly
The price is $180
Sep 8 - Sep 9
Total with taxes and fees
Riverfront Cabin with Private Dock
A compact RV kitchen with wooden cabinets, a stove, and a dining area with a bench.

17. 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 1 - Sep 2
Total with taxes and fees
Big River Escape Coyote Camper #1
A spacious living room with a grey sofa, a coffee table, and a patterned rug.

18. Big River Inn - 3 bedroom apartment in Alma

Big River Inn - 3 bedroom apartment in Alma
Alma
8.8 out of 10, Excellent, (22 reviews)
"Very enjoyable place…."
United States
Kelly D.
$309 nightly
The price is $345
Oct 1 - Oct 2
Total with taxes and fees
Big River Inn - 3 bedroom apartment in Alma
A garden with a bench and various plants.

19. The Hen House Retreat - A Comfortable Place to Roost

The Hen House Retreat - A Comfortable Place to Roost
Highland
9.6 out of 10, Exceptional, (103 reviews)
"Comfortable place, beautiful spot!"
United States
Grace D.
$186 nightly
The price is $200
Sep 1 - Sep 2
Total with taxes and fees
The Hen House Retreat - A Comfortable Place to Roost
An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

20. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (59 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
$269 nightly
The price is $309
Sep 1 - Sep 2
Total with taxes and fees
Riverfront Twin Home
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

Gundersen Hotel & Suites

Gundersen Hotel & Suites

10/10 Excellent
"Excellent Hotel everything clean, excellent staff and excellent service in breakfast."
Yamil 2-night trip
Posted 18 hours ago
Gundersen 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 $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 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 Altra Federal Credit Union Stadium 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.