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Search results; Over 1,000 homes in Winterset

Guest favourite
Home in Winterset
The Legacy Stone House
1 bedroom, 1 bed, 1 private bathroom
12–17 Jul
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4.95 out of 5 average rating, 329 reviews
Guest favourite
Home in Winterset
Rosehaven
3 bedrooms, 4 beds
19–24 Aug
4.98 out of 5 average rating, 122 reviews
Top guest favourite
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
2 bedrooms, 6 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 114 reviews
Top guest favourite
Home in Winterset
Debbie's Komfy Diggs Winter Set
2 bedrooms, 2 beds
23–28 Aug
4.97 out of 5 average rating, 335 reviews
Top guest favourite
Home in Winterset
The Little Red House
2 bedrooms, 4 beds
17–22 Jul
4.96 out of 5 average rating, 57 reviews
Top guest favourite
Flat in Winterset
Luxury Studio- 1 Block to Town Square
1 queen bed
10–15 Jul
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Home in Winterset
The Little Brick House - Walkable to the Square
2 bedrooms, 2 beds
7–12 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Winterset
Charming abode
3 bedrooms, 4 beds
13–18 Jul
4.72 out of 5 average rating, 25 reviews
Top guest favourite
Home in Winterset
Hygge House in the ❤️ of historic Winterset
3 bedrooms, 4 beds
18–23 Aug
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Apartment in Winterset
Luxury 2 Bed/2 Bath Condo-1 Block to Downtown
2 bedrooms, 2 queen beds
24–29 Aug
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Home in Winterset
​Cottage on Court: Historic Gem | 3 Blks to Square
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Flat in Winterset
The Suite Iowa Life
1 bedroom, 1 queen bed
19–24 Jul
4.94 out of 5 average rating, 401 reviews
Top guest favourite
Farm stay in Winterset
Entire farmhouse in the country
4 bedrooms, 5 beds
20–25 Aug
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Home in Winterset
The Roost at Speckled Hen Farms.
4 bedrooms, 4 beds
12–17 Jul
5.0 out of 5 average rating, 96 reviews
Top guest favourite
Flat in Winterset
Winterset Square Loft/Retreat
1 bedroom, 1 bed
19–24 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Winterset
Charming Winterset Vacation Rental w/ Yard & Patio
4 bedrooms, 5 beds
16–21 Aug
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Home in Winterset
Covered Bridge Haven - 3BR House w/ Themed Rooms
3 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Guest suite in Winterset
2 BR fully furnished private condo sleeps 4
2 bedrooms, 2 queen beds
17–22 Jul
4.87 out of 5 average rating, 134 reviews
Guest favourite
Home in Winterset
Farm Escape | 12 Guest | Walk to Holliwell Bridge
5 bedrooms, 7 beds
8–13 Aug
4.94 out of 5 average rating, 48 reviews