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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winona vacation rentals

A two-story house with a wooden staircase leading to a yellow door, a brick wall, and a window with a white frame.

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, (32 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
$171 nightly
The price is $190
Oct 5 - Oct 6
Total with taxes and fees
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
A modern apartment with a staircase, a dining area, and a living space.

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, (34 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
$266 nightly
The price is $286
Oct 5 - Oct 6
Total with taxes and fees
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
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
8.0 out of 10, Very good, (2 reviews)
"Parkview is a quaint bungalow one block off the Lake. Easy access to Downtown, Winona State and recreation. Lovely back yard and front porch. Plenty of party in front and back. Definitely will stay again."
United States
Mary T.
$230 nightly
The price is $254
Oct 5 - Oct 6
Total with taxes and fees
Parkside Pet Friendly Bungalow
A round glass table with two wicker chairs, a bottle, and two glasses of red wine on a metal tray.

4. Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN

Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN
Winona
10.0 out of 10, Exceptional, (150 reviews)
"Absolutely amazing! So much charm and space…could definitely stay here again!"
United States
Lynn B.
$449 nightly
The price is $498
Oct 5 - Oct 6
Total with taxes and fees
Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN
A field of lavender with a path leading through it.

5. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (46 reviews)
"Brady was very prompt and the stay exceeded expectations We plan to stay again very soon! Thank you, Brady!"
United States
Josias F.
$111 nightly
The price is $117
Oct 12 - Oct 13
Total with taxes and fees
Tamarack Point Homestead
A wooden deck with a bench, a white door, and hanging flower baskets.

6. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (105 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
$145 nightly
The price is $160
Oct 5 - Oct 6
Total with taxes and fees
The Bungaleau 1 Bedroom House In Cute Rivertown
A bunk bed room with a window view, a ceiling fan, and a TV.

7. 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.
$137 nightly
The price is $147
Oct 18 - Oct 19
Total with taxes and fees
Ridgetop Retreat Tiny Home, Dakota MN
A living room with a television, sofa, coffee table, and shelves with decorative items.

8. Vintage Lustron Home Piece of History

Vintage Lustron Home Piece of History
Minnesota City
10.0 out of 10, Exceptional, (36 reviews)
"A beautiful comfortable welcoming home!"
United States
Jocelyn R.
$199 nightly
The price is $214
Oct 5 - Oct 6
Total with taxes and fees
Vintage Lustron Home Piece of History
A wooden cabin with a porch, two chairs, and a door.

9. Tiny Treehouse Cabin | Bluff Woodlands #2

Tiny Treehouse Cabin | Bluff Woodlands #2
Elba
9.8 out of 10, Exceptional, (17 reviews)
"Beautiful area enjoyed our stay immensely"
United Kingdom
I.M l.
$179 nightly
The price is $192
Oct 5 - Oct 6
Total with taxes and fees
Tiny Treehouse Cabin | Bluff Woodlands #2
A spacious living room with a red sofa, a white coffee table, and a fireplace.

10. Farmhouse Apartment - River Road Historic Home

Farmhouse Apartment - River Road Historic Home
Fountain City
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful views, excellent location near several cute towns, plus Winona, which has lots of chain store shopping options. The trains were barely noticeable, personally I like the sound. Definitely recommend!"
United States
Katie B.
$223 nightly
The price is $235
Oct 13 - Oct 14
Total with taxes and fees
Farmhouse Apartment - River Road Historic Home
A compact RV kitchen with wooden cabinets, a stove, and a dining area with a bench.

11. Big River Escape Coyote Camper #1

Big River Escape Coyote Camper #1
Buffalo City
10.0 out of 10, Exceptional, (2 reviews)
"Awesome as usual "
United States
Matthew B.
$138 nightly
The price is $146
Oct 5 - Oct 6
Total with taxes and fees
Big River Escape Coyote Camper #1
Two wooden cabins elevated on stilts in a forest, with outdoor seating and hammocks.

12. Tiny Treehouse Cabin | Bluff Woodlands #1

Tiny Treehouse Cabin | Bluff Woodlands #1
Elba
9.6 out of 10, Exceptional, (10 reviews)
"Great area a place to stay. "
United States
Paul T.
$191 nightly
The price is $205
Oct 5 - Oct 6
Total with taxes and fees
Tiny Treehouse Cabin | Bluff Woodlands #1
A rustic wooden pavilion with picnic tables, surrounded by a gravel area and grassy lawn.

13. 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
Oct 7 - Oct 8
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.

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
Oct 5 - Oct 6
Total with taxes and fees
Badger Cabin w/ Lofts, Fireplace & WiFi
Exterior

15. 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.
$150 nightly
The price is $158
Oct 20 - Oct 21
Total with taxes and fees
Riverfront Cabin with Private Dock
A brick fireplace with a flat-screen TV above it, surrounded by potted plants and a leather couch.

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.
$552 nightly
The price is $585
Oct 6 - Oct 7
Total with taxes and fees
The Chateau on Butterfly Trail - 6 Bdrm Retreat
A bedroom with a bed, a nightstand, a lamp, and a window with curtains.

17. Hidden Gem - 1BR/1Bath in Lax WI

Hidden Gem - 1BR/1Bath in Lax WI
Holy Trinity-Longfellow
9.6 out of 10, Exceptional, (18 reviews)
"Our stay was perfect! The host was easy to communicate with and even let us check in early. The place was so cute! The bed was super comfortable and everything looked good and felt clean. Very safe area and neighborhood. Such a bonus to have a restaurant attached to the property! We will for sure stay here again!"
United States
Heather
$144 nightly
The price is $166
Oct 8 - Oct 9
Total with taxes and fees
Hidden Gem - 1BR/1Bath in Lax WI
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

18. 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, (68 reviews)
"I"
United States
Charlie
$148 nightly
The price is $170
Oct 22 - Oct 23
Total with taxes and fees
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
A spacious living room with a brown sofa, a round coffee table, and a patterned rug. There is a ceiling fan, a dining area with chairs, and a staircase leading to another level.

19. Hokah Ohana House: Historic charm, Modern updates

Hokah Ohana House: Historic charm, Modern updates
Hokah
10.0 out of 10, Exceptional, (39 reviews)
"Very comfortable and had everything you need to feel at home!"
United States
David R.
$170 nightly
The price is $181
Oct 13 - Oct 14
Total with taxes and fees
Hokah Ohana House: Historic charm, Modern updates
A garden with a bench and various plants.

20. 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, (104 reviews)
"Comfortable place, beautiful spot!"
United States
Grace D.
$186 nightly
The price is $200
Oct 5 - Oct 6
Total with taxes and fees
The Hen House Retreat - A Comfortable Place to Roost
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

The Charmant Hotel

The Charmant Hotel

10/10 Excellent
"Love it here"
Lea 2-night trip
Posted less than an hour ago
The Charmant Hotel

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 $160 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 13 vacation rentals for your stay in Winona.

What can I see and do in Winona?

Enjoy the outdoors at Sugar Loaf Bluff and Mississippi River, or simply take in cultural attractions like Minnesota Marine Art Museum and Pickwick Mill. While here, Great River Bluffs State Park and Winona Mall 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.