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Search results; Over 1,000 homes in Winterset

Descriptions are based on details hosts provide
Guest favourite
Home in Winterset
The Legacy Stone House
1 bedroom, 1 bed, 1 private bathroom
18–23 Jul
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4.95 out of 5 average rating, 329 reviews
Guest favourite
Home in Winterset
Walk to the square, near covered bridges
4.98 out of 5 average rating, 124 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
Top guest favourite
Flat in Winterset
Historic downtown loft with a writing office
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Aug
Top guest favourite
Flat in Winterset
Fireplace and Murphy bed near town square
4.94 out of 5 average rating, 31 reviews, 1 bed, 1 bathroom
20–25 Jul
Guest favourite
Home in Winterset
Charming abode
4.72 out of 5 average rating, 25 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
Top guest favourite
Loft in Winterset
Loft overlooking the historic downtown square
5.0 out of 5 average rating, 114 reviews, 2 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Winterset
Blocks from historic downtown Winterset
4.97 out of 5 average rating, 338 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Flat in Winterset
Country views, fire pit, and a grill
4.94 out of 5 average rating, 401 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Aug
Top guest favourite
Apartment in Winterset
Fireplace and a balcony, near downtown
4.97 out of 5 average rating, 35 reviews, 2 bedrooms, 2 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Home in Winterset
The Little Brick House - Walkable to the Square
5.0 out of 5 average rating, 23 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
7–12 Sept
Top guest favourite
Home in Winterset
A 70s ranch on 5 rolling acres
5.0 out of 5 average rating, 97 reviews, 4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Winterset
The Little Red House
4.96 out of 5 average rating, 57 reviews, 2 bedrooms, 4 beds, 1 bathroom
5–10 Aug
Top guest favourite
Home in Winterset
​Cottage on Court: Historic Gem | 3 Blks to Square
5.0 out of 5 average rating, 45 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
17–22 Aug
Top guest favourite
Home in Winterset
Hygge House in the ❤️ of historic Winterset
4.99 out of 5 average rating, 68 reviews, 3 bedrooms, 4 beds, 1 bathroom
11–16 Aug
Top guest favourite
Home in Winterset
Themed rooms near the covered bridges
5.0 out of 5 average rating, 24 reviews, 3 bedrooms, 4 beds, 3 bathrooms
3–8 Aug
Top guest favourite
Farm stay in Winterset
Entire farmhouse in the country
4.98 out of 5 average rating, 62 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Aug
Top guest favourite
Guest suite in Winterset
2 BR fully furnished private condo sleeps 4
4.87 out of 5 average rating, 134 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Jul
Guest favourite
Home in Winterset
Charming Winterset Vacation Rental w/ Yard & Patio
4.97 out of 5 average rating, 39 reviews, 4 bedrooms, 5 beds, 1.5 bathrooms
16–21 Aug
Guest favourite
Home in Winterset
Farm Escape | 12 Guest | Walk to Holliwell Bridge
4.94 out of 5 average rating, 48 reviews, 5 bedrooms, 7 beds, 2.5 bathrooms
8–13 Aug