Holiday Homes in Winona

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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

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 €161
includes taxes & fees
28 Jan - 29 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 €377
includes taxes & fees
18 Jan - 19 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 €267
includes taxes & fees
16 Jan - 17 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 €105
includes taxes & fees
28 Jan - 29 Jan
Tamarack Point Homestead
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 €175
includes taxes & fees
18 Jan - 19 Jan
The Hen House Retreat - A Comfortable Place to Roost
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 €279
includes taxes & fees
19 Jan - 20 Jan
French Island w/Hot Tub, Kayak, Lake View, EV
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 €271
includes taxes & fees
18 Jan - 19 Jan
Riverfront Twin Home
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 €136
includes taxes & fees
19 Jan - 20 Jan
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
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 €188
includes taxes & fees
24 Jan - 25 Jan
Vintage Lustron Home Piece of History
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 €290
includes taxes & fees
15 Feb - 16 Feb
Jake's Place
Living area

Holiday Home in Fountain City

Farmhouse Apartment - River Road Historic Home
9.8 out of 10, Exceptional, (18 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 €206
includes taxes & fees
27 Jan - 28 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)
"Great location, close to downtown, mall, river etc. very clean. Close to good coffee and restaurants. Great place"
United States
Dan M.
The price is €242
includes taxes & fees
18 Jan - 19 Jan
Great 1 Bedroom unit with easy access to everything
Exterior

Holiday Home in Historic Downtown La Crosse

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
9.8 out of 10, Exceptional, (52 reviews)
"Amazing house, great location, excellent host!"
United States
Ed R.
The price is €213
includes taxes & fees
18 Jan - 19 Jan
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Panoramic House | 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
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, (7 reviews)
"Wonderful stay! I loved the river view!"
United States
Dawn M.
The price is €401
includes taxes & fees
18 Jan - 19 Jan
Mississippi waterfront vacation home that welcomes dogs! Private dock for boats
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 €126
includes taxes & fees
19 Jan - 20 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 €527
includes taxes & fees
15 Feb - 16 Feb
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 €439
includes taxes & fees
19 Jan - 20 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.
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Top Winona Hotel Reviews

AmericInn by Wyndham Winona

AmericInn by Wyndham Winona

10/10 Excellent
"The hotel staff was welcoming. The room was clean and spacious. We enjoyed the free continental breakfast options."
Meredith 1-night trip
Posted 6 days ago
AmericInn by Wyndham Winona

Find out more about Winona

Winona Holiday Homes information

Number of reviews
580
Accommodation
98 Holiday Homes
Lowest Price
€105
Highest Price
€527