Holiday Homes in Winona

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

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 €164
includes taxes & fees
3 Mar - 4 Mar
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO
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 €265
includes taxes & fees
3 Mar - 4 Mar
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Outdoor dining

Holiday Home in Winona

Charming Brick Farmhouse with a Touch of Elegance. -Winona
10.0 out of 10, Exceptional, (138 reviews)
"Host was easy to work with and very accommodating. The house was great and the kitchen was well equipped."
United States
John W.
The price is €358
includes taxes & fees
3 Mar - 4 Mar
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Property grounds

Holiday Home in Arcadia

Tamarack Point Homestead
10.0 out of 10, Exceptional, (33 reviews)
"It is a lovely spot. Very relaxing. "
United States
Peggy K.
The price is €103
includes taxes & fees
3 Mar - 4 Mar
Tamarack Point Homestead
Property grounds

Holiday Home in La Crosse

French Island w/Hot Tub, Kayak, Lake View, EV
9.8 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay in this peaceful, quiet neighborhood."
United States
Colleen C.
The price is €260
includes taxes & fees
4 Mar - 5 Mar
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)
"It was the perfect weekend getaway!! "
United States
Theresa G.
The price is €257
includes taxes & fees
3 Mar - 4 Mar
Riverfront Twin Home
Smart TV, books

Holiday Home in Minnesota City

Vintage Lustron Home Piece of History
10.0 out of 10, Exceptional, (30 reviews)
"I loved staying here! The interior was comfortable, cozy, and fascinating! "
United States
melanie
The price is €182
includes taxes & fees
3 Mar - 4 Mar
Vintage Lustron Home Piece of History
Interior

Holiday Home in Holy Trinity-Longfellow

4 BR w/ Bluff Views | Snow-Dusted Escape
9.4 out of 10, Exceptional, (33 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 €369
includes taxes & fees
3 Mar - 4 Mar
4 BR w/ Bluff Views | Snow-Dusted Escape
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 €275
includes taxes & fees
3 Mar - 4 Mar
Jake's Place
Living area

Holiday Home in Fountain City

Farmhouse Apartment - River Road Historic Home
9.8 out of 10, Exceptional, (19 reviews)
"Great rental! Great location and very clean. Hidden gem!"
United States
Anthony y.
The price is €196
includes taxes & fees
3 Mar - 4 Mar
Farmhouse Apartment - River Road Historic Home
Property grounds

Holiday Home in Highland

The Hen House Retreat - A Comfortable Place to Roost
9.8 out of 10, Exceptional, (87 reviews)
"Very nice perfect for us, would rent again!"
United States
Mitchell G.
The price is €169
includes taxes & fees
10 Mar - 11 Mar
The Hen House Retreat - A Comfortable Place to Roost
Property grounds

Holiday Home in Northside

Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
9.8 out of 10, Exceptional, (50 reviews)
"Wonderful stay, super cozy, perfect for a getaway "
United States
Katie C.
The price is €134
includes taxes & fees
3 Mar - 4 Mar
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
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 €165
includes taxes & fees
3 Mar - 4 Mar
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, (55 reviews)
"Loved the home! Perfect girls weekend!"
United States
Helen H.
The price is €203
includes taxes & fees
3 Mar - 4 Mar
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
Exterior

Holiday Home in Onalaska

Large home space minutes from La Crosse
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 €133
includes taxes & fees
3 Mar - 4 Mar
Large home space minutes from La Crosse
Fridge, microwave, oven, stovetop

Holiday Home in Trempealeau

Spacious 4-bedroom home in Trempealeau, WI
9.6 out of 10, Exceptional, (4 reviews)
"House was clean and well stocked. Really enjoyed our stay"
United States
Richard N.
The price is €341
includes taxes & fees
16 Mar - 17 Mar
Spacious 4-bedroom home in Trempealeau, WI
Exterior

Holiday Home in Buffalo City

NEW Mississippi Riverfront Sunset House - family, friends & river come together
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 €501
includes taxes & fees
8 Mar - 9 Mar
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)
"Had a nice stay in Fountain City"
United States
David K.
The price is €608
includes taxes & fees
3 Mar - 4 Mar
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

GrandStay Hotel & Suites

GrandStay Hotel & Suites

10/10 Excellent
"Everything was nice "
Lisa 2-night trip
Posted 4 days ago
GrandStay Hotel & Suites

Find out more about Winona

Winona Holiday Homes information

Number of reviews
632
Accommodation
98 Holiday Homes
Lowest Price
€103
Highest Price
€608