
Holiday houses in Winona County
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Winona County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Winona County holiday rentals
Other great holiday rentals in Winona County
Guest favourite

Private room in Stockton
4.81 out of 5 average rating, 122 reviewsPeaceful Country Charm
RichardRating, 5 stars1 day ago
Tammy was very responsive both while on site and while away. Her husband also offered help when Tammy wasn’t around.
Guest favourite

Farm stay in Trempealeau
4.96 out of 5 average rating, 120 reviewsFrank’s Farmhouse at Ecker’s Apple Farm
JenniferRating, 5 stars2 weeks ago
We had a lovely weekend at the farmhouse. It was clean, cozy, well appointed and just the right size for our family! Jess and family were super helpful and responsive. The apple farm adjacent is beautiful as well and we had a nice walk between the apple trees in the morning. Just a sweet spot and a relaxing weekend!

Bungalow in Trempealeau
4.85 out of 5 average rating, 121 reviewsThe Bungaleau
WilliamRating, 5 stars2 weeks ago
The host was fast and helpful in his responses. We really appreciate the host’s helpful attitude. We liked the location because we wanted to bike the Great River Trail and the home could not be closer. There was a cool Reggae festival 2 blocks away and the river and hills were gorgeous. We will be back. This place is a very good spot and a great value.
Guest favourite

Barn in Winona
4.93 out of 5 average rating, 54 reviewsScrappin' on the Ranch
BrandonRating, 5 stars1 month ago
The barn and property were as advertised. Very peaceful and beautiful. Our stay was for a HS fishing tournament nearby so we didn’t get to fully utilize the property for its value as our schedule was full. It was a great place to come back to after a long day and made for a relaxing stay. Despite our short time here, we highly recommend this place to stay in the future.
Top Guest favourite

Tiny home in Houston
5 out of 5 average rating, 16 reviewsThe Guest Nest
JoAnnRating, 5 stars3 days ago
The Guest Nest is a perfect place to stay if you are looking for natural beauty. The highlight is the beautiful scenery including the cute cabin, tranquil valley, and wildlife ranging from fireflies to fawns.

Cabin in Winona
5 out of 5 average rating, 4 reviewsEsther’s Cottage
SandyRating, 5 stars1 day ago
We really enjoyed our stay at Esther's Cottage (and we'd really like to know more about Esther!) The home was beautiful, spacious, clean, and had everything we needed. The view is spectacular! We spent most of our time there in the sun room overlooking the river, playing games and enjoying the scenery. There is a nice porch also but it was too hot to sit out there on the weekend we visited! The new owners, David and Kara are very responsive and did everything they could to make sure we were comfortable. Would definitely stay here again!
Guest favourite

Private room in Trempealeau
4.83 out of 5 average rating, 191 reviewsPatty & Mike's Basement Level-close to Perrot Park
RuthRating, 5 stars1 day ago
Lovely location!! Patty was VERY responsive to inquiries. She even allowed us to check out a little later than the posted check-out time which was much appreciated. Great value! Loved the selection of beds available. Will definitely stay here again…
Top Guest favourite

Cottage in Altura
4.91 out of 5 average rating, 46 reviews1 Bedroom cabin in the White Water River Valley
LisaRating, 5 stars1 week ago
Our second time staying at Jon’s Airbnb and once again it was a great time. The house is as described/pictured and very clean. The location is excellent. Very close to Whitewater State Park. Only 20 min from Winona. There is an excellent restaurant down the road called Elba House Coffee and Spirits. Highly recommend stopping there for a meal while staying in Elba!
Destinations to explore
- Rentals with outdoor seating Winona County
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- Rentals with a fire pit Winona County
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