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Holiday Homes in Winona

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Featured Holiday Homes in Winona

Centrally Located House with the view on Bluffs and artist's outdoor studio.
9.2 out of 10, Wonderful, (16)
"The location of the house was great for an appointment we had in La Crosse. The backyard looked nice and I wish we would have been able to utilize it. One of the “bedrooms” is open to the living room, but that was fine for us. Overall it worked for what we needed. "
Centrally Located House with the view on Bluffs and artist's outdoor studio.
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
9.8 out of 10, Exceptional, (6)
"I absolutely loved this house and all of its charm. It was super welcoming and comfortable. "
The price is NZ$408
includes taxes & fees
29 Sept - 30 Sept
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
The Bungaleau 1 Bedroom House In Cute Rivertown
9.8 out of 10, Exceptional, (65)
"Cute cottage house walking distance to Mississippi and historic distric of Trempelau. Definitely would stay again."
The price is NZ$281
includes taxes & fees
7 Oct - 8 Oct
The Bungaleau 1 Bedroom House In Cute Rivertown
Bayfront Cottage is a 3 bedroom house on Richmond Bay.
8.4 out of 10, Very good, (20)
"Beds were comfortable. Everything was as stated exact y as the add. Thanks you"
Bayfront Cottage is a 3 bedroom house on Richmond Bay.
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
9.8 out of 10, Exceptional, (8)
"Perfect place right in town!"
The price is NZ$435
includes taxes & fees
30 Sept - 1 Oct
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Secluded Home - Views of Mississippi River remote location 15 min from La Crosse
10.0 out of 10, Exceptional, (141)
"Lots of room for our group of 6. Clean, Games. Great time for everyone."
Secluded Home - Views of Mississippi River remote location 15 min from La Crosse
The Hen House Retreat - A Comfortable Place to Roost
9.8 out of 10, Exceptional, (71)
"Very nice clean house. Wish we could have stayed longer. Plenty of room for everyone. "
The price is NZ$349
includes taxes & fees
29 Sept - 30 Sept
The Hen House Retreat - A Comfortable Place to Roost
Spacious Trempealeau Retreat
10.0 out of 10, Exceptional, (3)
"We were in town for a funeral. "
The price is NZ$733
includes taxes & fees
22 Oct - 23 Oct
Spacious Trempealeau Retreat
'RiverSong' Waterfront La Crosse Home w/ Dock
10.0 out of 10, Exceptional, (70)
"What a great place! Literally the cleanest, most organized vacation rental we’ve ever stayed in! Having the two living spaces upstairs and downstairs was great for our family. Gave our teens their own space to hang out while allowing my husband space to get zoom meetings in. Patios are amazing to enjoy the summer weather! Highly recommend!"
'RiverSong' Waterfront La Crosse Home w/ Dock
Country Charm Over River Valley And Horse Farm
10.0 out of 10, Exceptional, (31)
"We had a fantastic time here in La Crescent. 9 of us men had plenty of room and the house and property were very clean. The host was very communicative and answered any questions we had. I would recommend this for anyone!"
Country Charm Over River Valley And Horse Farm
Victorian era Mississippi riverview retreat.
9.6 out of 10, Exceptional, (22)
"This house was great! We were down to visit my son at Winona State University for the weekend. Fountain City was the perfect cute little river town and it was a short drive away. The house was cozy, clean, quiet, and well stocked. Beds were very comfortable and the host is very accomodating and always seeking to improve, which shows great character. We will definitely stay again! "
Victorian era Mississippi riverview retreat.
Family friendly in the peaceful heart of town
10.0 out of 10, Exceptional, (81)
"When we first walked into the place and fumbled for a light switch, we saw a marvelous kitchen where everything had a descriptive label. We were quickly able to bypass the usual "Hey, where are the silverware?" complications immediately. Multi-switch panels are also clearly labeled as to their function. Convenient! During the first afternoon we were there heavy rain came through while we were watching TV in the front room. We didn't notice the rain until someone got up to see it out the...
Family friendly in the peaceful heart of town
Cobblestone Cottage, 4 Bedroom, centrally located
10.0 out of 10, Exceptional, (13)
"We had 2 families, staying in LaCrosse for a memorial service. Our adult kids didn’t want to sleep in the same beds, but there was plenty of room on the floor of the bedrooms to blowup air mattresses so it worked out perfectly. The house is charming and centrally located with a great coffee shop only a five minute walk away, which was super convenient. We would absolutely stay here again."
Cobblestone Cottage, 4 Bedroom, centrally located
The Historic A.C. Carter House - River Romance on the La Crosse Historical Tour!
9.8 out of 10, Exceptional, (79)
"Just as described with great communication from host."
The Historic A.C. Carter House - River Romance on the La Crosse Historical Tour!
Great 1 Bedroom unit with easy access to everything
9.6 out of 10, Exceptional, (43)
"The duplex has been tastefully remodeled. The kitchen is well stocked. The AC worked well. The front porch was a quiet spot for morning coffee. Some tv sound was audible from the adjacent space. The queen bed was soft but comfortable. A king bed would fit in the space and would be nice. We enjoyed our 1 night stay at this convenient location. "
The price is NZ$321
includes taxes & fees
29 Sept - 30 Sept
Great 1 Bedroom unit with easy access to everything
Mississippi River View with updated driveway
9.4 out of 10, Exceptional, (122)
"We enjoyed the impressive views and spending time on the screened-in porch. (The views are more impressive than the photos show, especially at sunset!) Kitchen was well stocked with cookware and other kitchen items. It's a beautiful and scenic drive along the river to get there. The driveway is very steep, but there are a few pull off spots next to the road for easier parking. Thanks for the wonderful stay!"
Mississippi River View with updated driveway
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
A fully equipped home overlooking Mississippi River in a charming river town
9.8 out of 10, Exceptional, (43)
"House was just as described. Very clean. Exceptional views of the river. Excellent internet connection. We enjoyed the open kitchen/living room/dining room area, nice to he able to continue conversations while cooking. "
A fully equipped home overlooking Mississippi River in a charming river town
Large Secluded Country Home Minutes from Town
10.0 out of 10, Exceptional, (60)
"Our group had a great stay at this property over Labor Day weekend. It's in a great location on a beautiful piece of land. It was a busy weekend with most of the time in the house spent either sleeping or getting ready, but the place was great and fit all our needs and then some. Would definitely book this house again for future visits to La Crosse. "
Large Secluded Country Home Minutes from Town
Rural Winona Co. Guest House Getaway: Relax and Enjoy the Simple Things in Life
10.0 out of 10, Exceptional, (33)
"Greatvplace way nicer then could expect "
Rural Winona Co. Guest House Getaway: Relax and Enjoy the Simple Things in Life
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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
9.4 out of 10, Exceptional, (101)
"We had a great time in this lovely property. The location was very convenient to town, but you also felt out in the country with all the trees - great star gazing from the balcony!"
Creekside Cabin Getaway
Heritage hideaway-Secluded Log Cabin
10.0 out of 10, Exceptional, (350)
"Will we come back—A resounding YES! Heritage Hideaway has been our favorite vacation destination for years. Thank you, Laurie and Troy "
Heritage hideaway-Secluded Log Cabin
Big River Escape Riverside Cabins
3.0 star property
9.0 out of 10, Wonderful, (22)
"Loved the area. Cabins were close to the water. Beautiful area to go for a walk. Clean, friendly. We will be back! "
The price is NZ$259
includes taxes & fees
29 Sept - 30 Sept
Big River Escape Riverside Cabins
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.