Search Vacation Homes in Winona

  • 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
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

Our top choices for Winona vacation homes

Interior

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, (27 reviews)
"Beautiful home we had a wonderful stay!!!"
United States
Thomas L.
The price is AED 955
AED 1,174 total
includes taxes & fees
25 May - 26 May
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Outdoor dining

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, (141 reviews)
"Excellent home and area!"
United States
Tracy W.
The price is AED 1,157
AED 1,874 total
includes taxes & fees
31 May - 1 Jun
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Terrace/patio

The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (90 reviews)
"Great location. Has everything you need to stay."
United States
todd s.
The price is AED 459
AED 589 total
includes taxes & fees
25 May - 26 May
The Bungaleau 1 Bedroom House In Cute Rivertown
Outdoor dining

Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (49 reviews)
"It was the perfect weekend getaway!! "
United States
Theresa G.
The price is AED 551
AED 1,208 total
includes taxes & fees
3 Jun - 4 Jun
Riverfront Twin Home
Smart TV, books

Vintage Lustron Home Piece of History

Vintage Lustron Home Piece of History
Minnesota City
10.0 out of 10, Exceptional, (30 reviews)
"Every thing was great! We always enjoy staying here. The home was excellent and we had no issues."
United States
Lynda S.
The price is AED 496
AED 783 total
includes taxes & fees
19 May - 20 May
Vintage Lustron Home Piece of History
Interior

4BR Blooms Near Downtown

4BR Blooms Near Downtown
Holy Trinity-Longfellow
9.4 out of 10, Exceptional, (35 reviews)
"Our stay was very nice. Tina was excellent in responding to a few of our needs. Lovey home and nicely decorated."
United States
Mary B.
The price is AED 551
AED 1,677 total
includes taxes & fees
25 May - 26 May
4BR Blooms Near Downtown
Property grounds

Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (35 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveler
The price is AED 335
AED 431 total
includes taxes & fees
19 May - 20 May
Tamarack Point Homestead
Exterior detail

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, (89 reviews)
"Very nice perfect for us, would rent again!"
United States
Mitchell G.
The price is AED 595
AED 734 total
includes taxes & fees
21 May - 22 May
The Hen House Retreat - A Comfortable Place to Roost
Fridge, microwave, oven, stovetop

Great 1 Bedroom unit with easy access to everything

Great 1 Bedroom unit with easy access to everything
Lower Northside
9.6 out of 10, Exceptional, (53 reviews)
"We had a great time! The house was clean and comfortable, and the dining options nearby were fantastic. The house was centrally located to what we wanted to do around town, so it made a great place to stay! Thank you for the wonderful time. "
United States
Dylan R.
The price is AED 314
AED 699 total
includes taxes & fees
19 May - 20 May
Great 1 Bedroom unit with easy access to everything
Private kitchen

Jake's Place

Jake's Place
Powell-Poage-Hamilton
9.8 out of 10, Exceptional, (8 reviews)
"Great place, great location. Very clean & practical! "
United States
Cori C.
Jake's Place
Living area

Farmhouse Apartment - River Road Historic Home

Farmhouse Apartment - River Road Historic Home
Fountain City
10.0 out of 10, Exceptional, (21 reviews)
"Great rental! Great location and very clean. Hidden gem!"
United States
Anthony y.
The price is AED 496
AED 833 total
includes taxes & fees
26 May - 27 May
Farmhouse Apartment - River Road Historic Home
Exterior

FC River Retreat

FC River Retreat
Milton
The price is AED 895
AED 1,778 total
includes taxes & fees
19 May - 20 May
FC River Retreat
Exterior

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Historic Downtown La Crosse
9.8 out of 10, Exceptional, (62 reviews)
"Great communication with hostBeautiful historic home. Wonderful place to stay with a group. "
United States
Melissa W.
The price is AED 678
AED 872 total
includes taxes & fees
20 May - 21 May
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Property grounds

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, (59 reviews)
"Great property a short drive from downtown and campus, convenient to the highway. Lots of fun decor and a beautiful screened-in gazebo in the back yard. The neighborhood is nice, quiet, and safe. It was the perfect place for our graduation weekend stay! The only downsides were - broken dishwasher, broken water/ice dispenser in the fridge, and an unadjustable shower head. That being said, those were fairly minor things which did not affect the quality of our stay. This is a great place and...
United States
Damien
The price is AED 360
AED 625 total
includes taxes & fees
28 May - 29 May
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Panoramic House | Living area | Flat-screen TV

Big River Escape Grandview Manse

Big River Escape Grandview Manse
3.0 star property
Altura
10.0 out of 10, Exceptional, (4 reviews)
"It was very roomy and easily accessible. The views were amazing. Would recommend to anyone anytime!!"
United States
Greg
The price is AED 1,154
AED 1,239 total
includes taxes & fees
26 May - 27 May
Big River Escape Grandview Manse
TV

Discover ‘Riverview Radiance,' a 5BR Minneiska marvel where the Mississippi meets modern luxury. Perfect for large groups, this home boasts a fully-equipped kitchen, sprawling views, and a suite of entertainment options. Revel in comfort with plush

Discover ‘Riverview Radiance,' a 5BR Minneiska marvel where the Mississippi meets modern luxury. Perfect for large groups, this home boasts a fully-equipped kitchen, sprawling views, and a suite of entertainment options. Revel in comfort with plush
Minnieska
10.0 out of 10, Exceptional, (10 reviews)
"Awesome gathering space for a large family. Beautiful views of the river. Comfy beds and responsive owner!"
United States
Lisa N.
The price is AED 1,344
AED 1,649 total
includes taxes & fees
20 May - 21 May
Discover ‘Riverview Radiance,' a 5BR Minneiska marvel where the Mississippi meets modern luxury. Perfect for large groups, this home boasts a fully-equipped kitchen, sprawling views, and a suite of entertainment options. Revel in comfort with plush
Living area

Great River Road - Victorian Historic Home (1898)

Great River Road - Victorian Historic Home (1898)
Fountain City
9.0 out of 10, Wonderful, (8 reviews)
"Had a nice stay in Fountain City"
United States
David K.
The price is AED 1,653
AED 2,658 total
includes taxes & fees
26 May - 27 May
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.
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

The Charmant Hotel

The Charmant Hotel

10/10 Excellent
"Staff was friendly, room was historic but with modern amenities. I would definitely stay again!"
Maxwell 1-night trip
Posted 2 hours ago
The Charmant Hotel

Explore a world of travel with Expedia