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Compare 123 Vacation Homes in Winona with updated reviews, rates, and availability.

Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

9.6 out of 10, Exceptional, (18)
"This home was very cute and cozy. Decor was very cool. Communication was great! Would definitely stay here again. "
The price is SAR 368
SAR 509 total
includes taxes & fees
13 Apr - 14 Apr
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

10.0 out of 10, Exceptional, (3)
"This house was perfect for my weekend trip to Winona-I would consider booking again if I return to the area. The pictures were accurate to the space. Property access was simple and explained well. The space was clean and cozy and had everything I needed for a comfortable stay. Bed is firm, yet comfortable. Location is great and walkable to several eateries and shops. Minimal street noise from passing cars (and was not disruptive at all). I didn’t get to enjoy the backyard space due to weather...
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

Rural Winona Co. Guest House Getaway: Relax and Enjoy the Simple Things in Life

10.0 out of 10, Exceptional, (38)
"Nice place"
Rural Winona Co. Guest House Getaway: Relax and Enjoy the Simple Things in Life

River Front Property

10.0 out of 10, Exceptional, (87)
"We stayed at a wonderful Vrbo right on the river. It was a beautiful 3 bedroom flat with a 4 season room and a large deck. It had a stairway down to a fishing pier. We got there and it was 80 degrees. Beautiful fishing weather. We caught some walleye and perch. The next day the weather was horrrible. We couldn’t fish much but enjoyed the rental immensely. It is great for fishing, relaxing and so much more!! "
River Front Property

Riverfront Twin Home

10.0 out of 10, Exceptional, (20)
"Very clean. Great location. Well stocked kitchen. Very comfortable beds. Lots of walking trails nearby. Had a wonderful weekend. "
The price is SAR 563
SAR 1,213 total
includes taxes & fees
12 May - 13 May
Riverfront Twin Home

The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs

10.0 out of 10, Exceptional, (45)
"The BRD Nest was a great place for our big family group to stay. Plenty of bedrooms and baths for privacy and nice open common areas for gathering. Can’t beat the view of the river from the windows and deck! "
The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs

Cozy 4 bedroom relax atmosphere enjoy beauty of bluff country driftless region

10.0 out of 10, Exceptional, (17)
"This was the perfect place for a relaxing weekend away from the daily stresses of life."
Cozy 4 bedroom relax atmosphere enjoy beauty of bluff country driftless region

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

9.8 out of 10, Exceptional, (22)
"The house is lovely, historic and well furnished. We spent as very comfortable weekend (12 adults) and enjoyed our time in the house as much as we did in the lovely town of LaCrosse."
The price is SAR 732
SAR 945 total
includes taxes & fees
15 Apr - 16 Apr
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!

10.0 out of 10, Exceptional, (30)
"We loved all of the space; everyone had their own room. Very clean and my daughter lives cooking in the kitchen! The Nature Place and walking paths just down the road are lovely! Beth had little snacks and chocolates around that the kids appreciated! Would definitely come back!"
The price is SAR 563
SAR 1,476 total
includes taxes & fees
22 Apr - 23 Apr
Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!

Spacious 4-bedroom home in Trempealeau, WI

9.0 out of 10, Wonderful, (2)
"Very nice and very comfortable. The coffee pot is very slow when brewing"
The price is SAR 563
SAR 1,635 total
includes taxes & fees
22 Apr - 23 Apr
Spacious 4-bedroom home in Trempealeau, WI

Charming 3-bedroom house with WiFi and AC in beautiful La Crosse

10.0 out of 10, Exceptional, (1)
"Home is located in a great area with all the amenities needed. Very nice home!"
Charming 3-bedroom house with WiFi and AC in beautiful La Crosse

Mississippi waterfront vacation home that welcomes dogs! Private dock for boats

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a wonderful stay and our host was great! Wonderful property with everything we needed for a fun, stress-free stay. Three bedrooms, each with its own bath, was ideal! The great room was perfect for group, sit-down dinners and party games!"
Mississippi waterfront vacation home that welcomes dogs! Private dock for boats

Bluffside cottage with gorgeous river views

10.0 out of 10, Exceptional, (25)
"The property was very clean, cozy, and comfortable with great views of the river and the town of Fountain City. We loved the porch and close proximity to many state parks and hiking trails. Would highly recommend this place to others."
Bluffside cottage with gorgeous river views

8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

10.0 out of 10, Exceptional, (133)
"3 couples enjoying a weekend away :) "
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

Within walking distance of all the amenities! Bike the trail~ float the river

10.0 out of 10, Exceptional, (11)
"We all talked about how clean and relaxing the home was…very clean, updated, well stocked and awesome location. "
Within walking distance of all the amenities! Bike the trail~ float the river

Family friendly in the peaceful heart of town

10.0 out of 10, Exceptional, (88)
"Beautiful house, close to the lake. Had everything you could need."
Family friendly in the peaceful heart of town

“The Cabin” on French Island

9.0 out of 10, Wonderful, (21)
"Within walking distance for food and convenience items. This house fit our needs well. We were there to ice fish. "
“The Cabin” on French Island

French Island Bungalow w/Hot Tub, Kayak, Lake View, EV Charger

10.0 out of 10, Exceptional, (12)
"We needed a place for the weekend and this house was perfect! Everything was very nice and clean. Everyone had their own space and my son even used the hot tub. Our dog loved walking through the neighborhood. Would definitely recommend. "
French Island Bungalow w/Hot Tub, Kayak, Lake View, EV Charger

Large Secluded Country Home Minutes from Town

10.0 out of 10, Exceptional, (66)
"We came for the state ski racing championships, The property was perfect only minutes from the hill. We appreciate all of her timely responses. Access to the garage was a tremendous benefit Thank you"
Large Secluded Country Home Minutes from Town

Entire high-quality lodge well equipped and tranquil - See ALBINO deer!

10.0 out of 10, Exceptional, (75)
"Great communication with the owners and the place was extremely clean! I hope I get the chance to stay here again! "
Entire high-quality lodge well equipped and tranquil - See ALBINO deer!
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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Other property types in Winona

The Broadway Exchange

10.0 out of 10, Exceptional, (23)
"Nice location house clean but dusty in spots"
The Broadway Exchange

Family friendly in the peaceful heart of town

10.0 out of 10, Exceptional, (88)
"Beautiful house, close to the lake. Had everything you could need."
Family friendly in the peaceful heart of town

Charming Brick Farmhouse with a Touch of Elegance. -Winona

10.0 out of 10, Exceptional, (123)
"I can’t say enough great things about this place! We started out our time on the patio with plenty of seating for our group. The kitchen was well stocked. We loved the Keurig with fun variety of coffees, plus a regular coffee maker. Main room had nice areas for conversations, watching the game and working on a family puzzle. Bedrooms with their own bathrooms was fantastic. Location is great. Beautiful area. Next time we get together this will be our place to stay. "
The price is SAR 1,127
SAR 1,847 total
includes taxes & fees
13 Apr - 14 Apr
Charming Brick Farmhouse with a Touch of Elegance. -Winona
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.