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
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Winona holiday homes

Exterior detail

Holiday Home in Historic Downtown Winona

Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO
10.0 out of 10, Exceptional, (20 reviews)
"Had everything we needed and great communication for our weekend stay. "
United States
Tanya G.
The price is HK$1,170
HK$1,427 total
includes taxes & fees
20 Jan - 21 Jan
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO
Outdoor dining

Holiday Home in Winona

Charming Brick Farmhouse with a Touch of Elegance. -Winona
10.0 out of 10, Exceptional, (138 reviews)
"Beautiful home! Close to SMU campus. "
United States
Lucy M.
The price is HK$1,930
HK$3,336 total
includes taxes & fees
20 Jan - 21 Jan
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Interior

Holiday Home in Winona

Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
10.0 out of 10, Exceptional, (26 reviews)
"Beautiful home we had a wonderful stay!!!"
United States
Thomas L.
The price is HK$2,027
HK$2,383 total
includes taxes & fees
20 Jan - 21 Jan
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Property grounds

Holiday Home in Arcadia

Tamarack Point Homestead
10.0 out of 10, Exceptional, (32 reviews)
"It is a lovely spot. Very relaxing. "
United States
Peggy K.
The price is HK$711
HK$915 total
includes taxes & fees
20 Jan - 21 Jan
Tamarack Point Homestead
Property grounds

Holiday Home in La Crosse

French Island w/Hot Tub, Kayak, Lake View, EV
10.0 out of 10, Exceptional, (19 reviews)
"Enjoyed our stay in this peaceful, quiet neighborhood."
United States
Colleen C.
The price is HK$1,014
HK$2,467 total
includes taxes & fees
25 Jan - 26 Jan
French Island w/Hot Tub, Kayak, Lake View, EV
Property grounds

Holiday Home in Highland

The Hen House Retreat - A Comfortable Place to Roost
9.8 out of 10, Exceptional, (87 reviews)
"The house is charming. We had a pleasant stay."
United States
Susan D.
The price is HK$1,263
HK$1,549 total
includes taxes & fees
20 Jan - 21 Jan
The Hen House Retreat - A Comfortable Place to Roost
Smart TV, books

Holiday Home in Minnesota City

Vintage Lustron Home Piece of History
10.0 out of 10, Exceptional, (29 reviews)
"I loved staying here! The interior was comfortable, cozy, and fascinating! "
United States
melanie
The price is HK$1,053
HK$1,662 total
includes taxes & fees
20 Jan - 21 Jan
Vintage Lustron Home Piece of History
Outdoor dining

Holiday Home in La Crosse

Riverfront Twin Home
10.0 out of 10, Exceptional, (44 reviews)
"Great place to stay! Had everything we needed!"
United States
Angie C.
The price is HK$1,053
HK$2,376 total
includes taxes & fees
20 Jan - 21 Jan
Riverfront Twin Home
Private kitchen

Holiday Home in Powell-Poage-Hamilton

Jake's Place
9.8 out of 10, Exceptional, (8 reviews)
"Great place, great location. Very clean & practical! "
United States
Cori C.
The price is HK$1,170
HK$2,564 total
includes taxes & fees
20 Jan - 21 Jan
Jake's Place
Property grounds

Holiday Home in Northside

Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
9.8 out of 10, Exceptional, (46 reviews)
"Wonderful stay, super cozy, perfect for a getaway "
United States
Katie C.
The price is HK$764
HK$1,282 total
includes taxes & fees
25 Jan - 26 Jan
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Living area

Holiday Home in Fountain City

Farmhouse Apartment - River Road Historic Home
9.8 out of 10, Exceptional, (19 reviews)
"It was very relaxing. We arrived late in the afternoon and had to leave early the next morning. My siblings and I all wished we had been able to have another day there."
United States
Lynn M.
The price is HK$1,053
HK$1,834 total
includes taxes & fees
20 Jan - 21 Jan
Farmhouse Apartment - River Road Historic Home
Fridge, microwave, oven, stovetop

Holiday Home in Lower Northside

Great 1 Bedroom unit with easy access to everything
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 HK$1,053
HK$1,973 total
includes taxes & fees
20 Jan - 21 Jan
Great 1 Bedroom unit with easy access to everything
Living area

Holiday Home in Altura

Big River Escape Grandview Manse
3.0 star property
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 HK$2,555
HK$2,744 total
includes taxes & fees
25 Jan - 26 Jan
Big River Escape Grandview Manse
Living area

Holiday Home in Brownsville

Mississippi waterfront vacation home that welcomes dogs! Private dock for boats
2.0 star property
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful stay! I loved the river view!"
United States
Dawn M.
The price is HK$2,339
HK$3,550 total
includes taxes & fees
19 Feb - 20 Feb
Mississippi waterfront vacation home that welcomes dogs! Private dock for boats
Exterior

Holiday Home in Historic Downtown La Crosse

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
9.8 out of 10, Exceptional, (53 reviews)
"Amazing house, great location, excellent host!"
United States
Ed R.
The price is HK$1,439
HK$1,870 total
includes taxes & fees
20 Jan - 21 Jan
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Exterior

Holiday Home in Onalaska

Large home space minutes from La Crosse
2.0 star property
6.0 out of 10, (1 review)
"Pros: Good Host, great value and location, pet friendly, cleanCons: Listing said entire home, so did not realize host would be on the property. Listing should have mentioned kids that are very loud during our stay. Understandable with kids, but note should have been made as two people were unable to sleep. Not much room for parking with host’s vehicles. More clarity and details on the listing would significantly help."
United States
Dylan M.
The price is HK$624
HK$1,111 total
includes taxes & fees
20 Jan - 21 Jan
Large home space minutes from La Crosse
Exterior

Holiday Home in Buffalo City

NEW Mississippi Riverfront Sunset House - family, friends & river come together
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay at this riverhouse! The home is modern, clean, and luxurious throughout, but the real surprise was the incredible garage entertainment space — part man cave, part clubhouse, and truly unlike anything we’ve seen in a vacation rental. We spent hours enjoying the putting green, shuffleboard table, and bar area - the huge TV was perfect for watching the Packers game!The sunsets over the river were absolutely incredible — truly the perfect way to end each day.This place is a...
United States
Anna M.
The price is HK$3,119
HK$4,697 total
includes taxes & fees
28 Jan - 29 Jan
NEW Mississippi Riverfront Sunset House - family, friends & river come together
Living area

Holiday Home in Fountain City

Great River Road - Victorian Historic Home (1898)
9.4 out of 10, Exceptional, (6 reviews)
"It is a great historical home with large rooms. It was very clean. We had a awesome stay."
United States
Jeff M.
The price is HK$1,980
HK$3,800 total
includes taxes & fees
20 Jan - 21 Jan
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

GrandStay Hotel & Suites

GrandStay Hotel & Suites

10/10 Excellent
"Wonderful staff that was very pleasant and helpful. Clean room's with all the amenities you need. Great location. I would recommend if visiting in the la crosse area."
John 2-night trip
Posted 4 days ago
GrandStay Hotel & Suites

Find out more about Winona

Winona Vacation Homes information

Number of reviews
581
Accommodation
98 Vacation Homes
Lowest Price
HK$915
Highest Price
HK$4,697

Explore a world of travel with Expedia