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

Winona Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

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.
The price is AED 551
AED 698 total
includes taxes & fees
5 Oct - 6 Oct
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
The price is AED 859
AED 1,052 total
includes taxes & fees
4 Oct - 5 Oct
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.
The price is AED 797
AED 981 total
includes taxes & fees
5 Oct - 6 Oct
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.
The price is AED 1,074
AED 1,831 total
includes taxes & fees
4 Oct - 5 Oct
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.
The price is AED 335
AED 431 total
includes taxes & fees
8 Oct - 9 Oct
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.
The price is AED 459
AED 589 total
includes taxes & fees
4 Oct - 5 Oct
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.
The price is AED 441
AED 553 total
includes taxes & fees
19 Oct - 20 Oct
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.
The price is AED 496
AED 787 total
includes taxes & fees
12 Oct - 13 Oct
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.
The price is AED 432
AED 706 total
includes taxes & fees
4 Oct - 5 Oct
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.
The price is AED 496
AED 864 total
includes taxes & fees
13 Oct - 14 Oct
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.
The price is AED 433
AED 535 total
includes taxes & fees
4 Oct - 5 Oct
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.
The price is AED 472
AED 753 total
includes taxes & fees
4 Oct - 5 Oct
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.
The price is AED 498
AED 603 total
includes taxes & fees
20 Oct - 21 Oct
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.
The price is AED 563
AED 680 total
includes taxes & fees
4 Oct - 5 Oct
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.
The price is AED 477
AED 580 total
includes taxes & fees
20 Oct - 21 Oct
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.
The price is AED 1,298
AED 2,200 total
includes taxes & fees
4 Oct - 5 Oct
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
The price is AED 400
AED 608 total
includes taxes & fees
4 Oct - 5 Oct
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
The price is AED 441
AED 722 total
includes taxes & fees
2 Nov - 3 Nov
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)
"Host very responsive, the accommodations were impeccably clean, great location and the layout was perfect for families!"
United States
Dia F.
The price is AED 307
AED 662 total
includes taxes & fees
26 Oct - 27 Oct
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.
The price is AED 595
AED 734 total
includes taxes & fees
4 Oct - 5 Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winona Hotel Reviews

Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

8/10 Good
"The property was very good and the staff was very helpful. We enjoyed the stay. We would not hesitate to stay here again."
Louise 1-night trip
Posted 6 hours ago
Express Suites Riverport Inn & Suites

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.