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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare 89 Vacation Homes in Winona with updated reviews, rates, and availability.

River Front Property
Beautiful view of the Black River

River Front Property

10.0 out of 10, Exceptional, (84)
"If you’re looking for a relaxing place, that is clean, a great fishing spot, quiet, but still close to everything, this is the place for you! Owner was very nice and the home was just as explained, very clean and comfortable. "
River Front Property
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Exterior

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

9.8 out of 10, Exceptional, (15)
"This property offers a great space for collaboration and team building. "
The price is AED 716
AED 925 total
includes taxes & fees
3 Mar - 4 Mar
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Bluffside cottage with gorgeous river views
View of Mississippi River from upper deck

Bluffside cottage with gorgeous river views

10.0 out of 10, Exceptional, (21)
"So cute/quiet/clean with gorgeous views of the river!"
Bluffside cottage with gorgeous river views
Mississippi waterfront vacation home that welcomes dogs! Private dock for boats
Exterior

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
Enjoy this newly remodeled house located on Lake Onalaska.
Kitchen

Enjoy this newly remodeled house located on Lake Onalaska.

10.0 out of 10, Exceptional, (112)
"Perfect location and accommodations for week long fishing excursion for 2 guys. Cleaning station in basement was perfect! Will stay again"
Enjoy this newly remodeled house located on Lake Onalaska.
Eclectic Retro Cottage in La Crosse, Blocks away from Mississippi River
Living area

Eclectic Retro Cottage in La Crosse, Blocks away from Mississippi River

9.6 out of 10, Exceptional, (12)
"We spent the day exploring around Lacrosse and traveling along Hwy 35. Very comfortable accommodation ‼️"
The price is AED 382
AED 524 total
includes taxes & fees
3 Mar - 4 Mar
Eclectic Retro Cottage in La Crosse, Blocks away from Mississippi River
“The Cabin” on French Island
Room

“The Cabin” on French Island

9.0 out of 10, Wonderful, (20)
"Great location. Right across from bait shop. Plenty of room"
“The Cabin” on French Island
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Welcome to the Village House Inn. Whole house vacation rental.

Charming Brick Farmhouse with a Touch of Elegance. -Winona

10.0 out of 10, Exceptional, (120)
"Our family stayed at the Village House Inn over Christmas and it was perfect for accommodating a large group very comfortably. The location and proximity to Winona was also ideal. We will definitely be back! "
The price is AED 1,194
AED 1,917 total
includes taxes & fees
11 Feb - 12 Feb
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Exterior

Charming 3-bedroom, 2 bathroom house with outdoor space in Winona

10.0 out of 10, Exceptional, (11)
"the inside was beautiful. the neighborhood was decent and quiet. very comfortable stay!"
The price is AED 863
AED 1,045 total
includes taxes & fees
11 Feb - 12 Feb
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Secluded Home - Views of Mississippi River remote location 15 min from La Crosse
Living area

Secluded Home - Views of Mississippi River remote location 15 min from La Crosse

10.0 out of 10, Exceptional, (148)
"This is our 3rd time staying here. It's a great spot to come down to see our grown kid and have everyone around. Enough to do in the house to not get bored if the weather is bad. Will be back as always. "
Secluded Home - Views of Mississippi River remote location 15 min from La Crosse
Large Secluded Country Home Minutes from Town
A large deck and covered patio overlooking the Coulee Bluffs

Large Secluded Country Home Minutes from Town

10.0 out of 10, Exceptional, (64)
"Comfy, clean and plenty of space for 6"
Large Secluded Country Home Minutes from Town
Charming 2-bedroom house on the Bay
Interior

Charming 2-bedroom house on the Bay

The price is AED 382
AED 763 total
includes taxes & fees
3 Mar - 4 Mar
Charming 2-bedroom house on the Bay
Cozy 4 bedroom relax atmosphere enjoy beauty of bluff country driftless region
Room

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

10.0 out of 10, Exceptional, (15)
"Cozy place, Lisa made it very welcoming for Xmas"
Cozy 4 bedroom relax atmosphere enjoy beauty of bluff country driftless region
Comfy Cottage
Living area

Comfy Cottage

9.8 out of 10, Exceptional, (27)
"Very clean, very new feeling, very nice place. Will be staying here again!"
Comfy Cottage
The Historic A.C. Carter House - River Romance on the La Crosse Historical Tour!
The Historic A.C. Carter House Walking Distance to River Fun!

The Historic A.C. Carter House - River Romance on the La Crosse Historical Tour!

9.6 out of 10, Exceptional, (81)
"Just as described with great communication from host."
The Historic A.C. Carter House - River Romance on the La Crosse Historical Tour!
Tamarack Point Homestead
Exterior

Tamarack Point Homestead

10.0 out of 10, Exceptional, (23)
"Lovely property, super clean, and so many nice, unexpected amenities!"
The price is AED 353
AED 449 total
includes taxes & fees
3 Mar - 4 Mar
Tamarack Point Homestead
Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!
Living area

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

10.0 out of 10, Exceptional, (27)
"We usually spend New Year's with family in LaCrosse. Family's recent move brought us to this part of town, and a VRBO with a yard for the dog seemed the best option. This house was perfect for our needs: room for everyone, beds for everyone, full kitchen with large refrigerator, within walking distance of family, large park nearby (although we only walked the dog there--too cold to play), fully fenced-in yard to let the dog out when returning late and again early in the morning when wanting to...
The price is AED 566
AED 1,461 total
includes taxes & fees
18 Feb - 19 Feb
Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse
8th Street Blues!

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

10.0 out of 10, Exceptional, (127)
"Our family appreciated having a warm, comfortable home to relax in, and visit while we were together. The 8th Street Blues house was fully stocked, had a fun scavenger hunt and is easy to get around to places. It’s located in a nice neighborhood. Check-in and out was very easy and communication was always fast and friendly. I highly recommend staying here! Chris and Sheila put a lot of thought and care into their home for their guests. Thank you for a wonderful experience! Stacey N"
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse
Within walking distance of all the amenities! Bike the trail~ float the river
Exterior

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

10.0 out of 10, Exceptional, (10)
"The house was great! Kitchen is well stocked and we felt right at home. We would love to come back again!"
Within walking distance of all the amenities! Bike the trail~ float the river
Bayfront Cottage is a 3 bedroom house on Richmond Bay.
Property grounds

Bayfront Cottage is a 3 bedroom house on Richmond Bay.

8.2 out of 10, Very Good, (30)
"This is a gorgeous house and perfect for my family of 5. We had a great stay and enjoyed the hosts friendly messaging and quick responses. Great location and space. "
Bayfront Cottage is a 3 bedroom house on Richmond Bay.
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

Charming Brick Farmhouse with a Touch of Elegance. -Winona
Welcome to the Village House Inn. Whole house vacation rental.

Charming Brick Farmhouse with a Touch of Elegance. -Winona

10.0 out of 10, Exceptional, (120)
"Our family stayed at the Village House Inn over Christmas and it was perfect for accommodating a large group very comfortably. The location and proximity to Winona was also ideal. We will definitely be back! "
The price is AED 1,194
AED 1,917 total
includes taxes & fees
11 Feb - 12 Feb
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater
Outdoor spa tub

Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater

2.0 star property
10.0 out of 10, Exceptional, (5)
"Very large, nice place to stay for all ages"
Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater
Heritage hideaway-Secluded Log Cabin
Property grounds

Heritage hideaway-Secluded Log Cabin

10.0 out of 10, Exceptional, (362)
"In the below zero weather, we were greeted with a fire roaring in the wood burning fireplace and an immaculate and inviting log cabin well equipped for our 4-day stay. Troy checked in with us on our first afternoon to make sure all was good. It was! We thoroughly enjoyed the cozy feel of the cabin and the giant supply of wood to keep the fire burning. There was also a heater that would back up the warmth if the fire burned low overnight. We can’t wait to come again in every season!"
Heritage hideaway-Secluded Log Cabin
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.