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Compare 86 Vacation Homes in Winona with updated reviews, rates, and availability.

Bayfront Cottage is a 3 bedroom house on Richmond Bay.
Property grounds

Bayfront Cottage is a 3 bedroom house on Richmond Bay.

8.4 out of 10, Very Good, (26)
"We were up in the are for Oktoberfest Race Weekend at Lacrosse Fairgrounds Speedway. Property had everything you needed, as we were not there a ton. Just sleeping and showers. Would be a great place during the summer, with a riverfront back yard, and plenty of space to hang out and have a fire, etc."
Bayfront Cottage is a 3 bedroom house on Richmond Bay.
Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater
Living area

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

2.0 star property
10.0 out of 10, Exceptional, (1)
Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater
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, (109)
"Quiet, cozy, clean, easy to locate and in centet of all towns, trails and parks."
Enjoy this newly remodeled house located on Lake Onalaska.
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, (9)
"What a wonderful home for us to bring are adult children together at for a weekend in LaCrosse. The bedrooms and bathrooms are spacious. The kitchen if excellent for making a family meal. The piano was an added surprise! Thanks Matt! We hope to be back!"
The price is AED 716
AED 934 total
includes taxes & fees
26 Nov - 27 Nov
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Riverfront Twin Home
Living area

Riverfront Twin Home

10.0 out of 10, Exceptional, (18)
"The place was very clean and conveniently located to downtown. "
The price is AED 551
AED 1,208 total
includes taxes & fees
26 Nov - 27 Nov
Riverfront Twin Home
A fully equipped home overlooking Mississippi River in a charming river town
Welcome to Trempealeau and the mighty Mississippi River!

A fully equipped home overlooking Mississippi River in a charming river town

9.8 out of 10, Exceptional, (47)
"Well-appointed home, lots of room, beautiful views, excellent access to park/trails/river."
A fully equipped home overlooking Mississippi River in a charming river town
Quirky Retro Cottage in La Crosse, Blocks away from Mississippi River
Room

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

9.8 out of 10, Exceptional, (11)
"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
8 Dec - 9 Dec
Quirky Retro Cottage in La Crosse, Blocks away from Mississippi River
Comfy Cottage
Living area

Comfy Cottage

10.0 out of 10, Exceptional, (25)
"We had a very nice nice stay, we were very pleased wirh the property. Only problem I had is that I was unable to get my booking on my phone and we never got wifi password until the day before we left. Very nice property we would rent again next year if we come back for October fest 2025"
Comfy Cottage
River Front Property
Beautiful view of the Black River

River Front Property

9.8 out of 10, Exceptional, (78)
"This property was perfect for my family. Large open rooms with large windows. My kids enjoyed the rotary phone that actually worked. They had never seen one before. Overall, our experience was great. We will definitely come back when we come back to this area. The host was very prompt with their reply to our questions. Highly recommend this property "
River Front Property
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!
Logde sleeps 11 ...set up for exploring the Mississippi River or Driftless Area.
Dining

Logde sleeps 11 ...set up for exploring the Mississippi River or Driftless Area.

10.0 out of 10, Exceptional, (42)
"It is conveniently located; excellent hosts; property is great."
The price is AED 606
AED 729 total
includes taxes & fees
13 Dec - 14 Dec
Logde sleeps 11 ...set up for exploring the Mississippi River or Driftless Area.
“The Cabin” on French Island
Room

“The Cabin” on French Island

9.0 out of 10, Wonderful, (19)
"It was nice. Cozy"
“The Cabin” on French Island
The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs
Property grounds

The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs

10.0 out of 10, Exceptional, (41)
"View and spacious rooms and bedrooms! Every couple loved having a bathroom, with family it was fine using the 5th bathroom in another’s bedroom which had the 5th bathroom. Loved the balcony around most of the house. Sister in law locked us out of the house but management was able to solve the issue immediately, what a lifesaver to get a tired family after a wedding into the house. Wish we had more time there to be with bothers and sisters. "
The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs
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, (123)
"Great stay at a great place. Cozy, welcoming, well stocked and comfortable. "
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse
Capeside Cottage
Exterior

Capeside Cottage

9.8 out of 10, Exceptional, (10)
"The place was better than advertised. Great location with a view of Grandad Bluff Well maintained with all the amenities Highly recommend this VRBO."
Capeside Cottage
Winter Wonderland Near UW | Warm Modern Haven
La Crosse has some of the most beautiful sunsets!

Winter Wonderland Near UW | Warm Modern Haven

9.6 out of 10, Exceptional, (23)
"We had a great time in La Crosse. The house was great for our needs. My little one appreciated the basement where he had more room to run around. The layout was a bit more tight than I imagined but we were all comfortable."
Winter Wonderland Near UW | Warm Modern Haven
French Island Bungalow w/Hot Tub, Kayak, Lake View, EV Charger
Please make yourself at home!

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

10.0 out of 10, Exceptional, (9)
"We had a wonderful time, the house is just like the pictures only better. I brought my eldry parents to visit my moms sister. The house was perfect for them. The backyard was nice, we even enjoyed some light fall flowers. I did enjoy the hot tub. Very quiet, peaceful setting."
French Island Bungalow w/Hot Tub, Kayak, Lake View, EV Charger
MCR is a property that features seclusion and privacy that is hard to find.

MCR is a property that features seclusion and privacy that is hard to find.

10.0 out of 10, Exceptional, (80)
"Money Creek Ranch is simply amazing. The house and property were absolutely incredible for our family to check out and be out in nature. The house is the most well equipped VRBO we’ve stayed in. Lots for the kids to do in the house, and seemingly endless trails to explore outside. We’ll definitely be back. "
MCR is a property that features seclusion and privacy that is hard to find.
Farmhouse Apartment - Great River Road Historic Home (1898)
Amazing Mississippi River views from the sun-room

Farmhouse Apartment - Great River Road Historic Home (1898)

9.8 out of 10, Exceptional, (11)
"My long time friend and I decided to get away for a few days, it was at last minute idea. We decided to go to Fountain City/Winona area to be by the river and see that part of Wisconsin/Mn. Enjoyed our time to relax and shop. The Farmhouse apartment is very nice and is exactly as described. If you love old charm in a small town, you will enjoy your stay. "
The price is AED 536
AED 904 total
includes taxes & fees
9 Dec - 10 Dec
Farmhouse Apartment - Great River Road Historic Home (1898)
Victorian era Mississippi riverview retreat.
Property grounds

Victorian era Mississippi riverview retreat.

9.6 out of 10, Exceptional, (23)
"It was a great HQ and place to sleep and relax. "
Victorian era Mississippi riverview retreat.
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

Creekside Cabin Getaway

Creekside Cabin Getaway

9.4 out of 10, Exceptional, (104)
"Weather was better than good for autumn in Minnesota, lots of trails to walk, only disappointment was the main reason we went down, to check out the Maritime Art Museum, not impressed."
Creekside Cabin Getaway
Bayfront Cottage is a 3 bedroom house on Richmond Bay.
Property grounds

Bayfront Cottage is a 3 bedroom house on Richmond Bay.

8.4 out of 10, Very Good, (26)
"We were up in the are for Oktoberfest Race Weekend at Lacrosse Fairgrounds Speedway. Property had everything you needed, as we were not there a ton. Just sleeping and showers. Would be a great place during the summer, with a riverfront back yard, and plenty of space to hang out and have a fire, etc."
Bayfront Cottage is a 3 bedroom house on Richmond Bay.
Heritage hideaway-Secluded Log Cabin
Front patio area with charcoal grill

Heritage hideaway-Secluded Log Cabin

10.0 out of 10, Exceptional, (357)
"It was a great stay. Best stay iv had using Vrbo. The property is perfect. "
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.