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Search results; Over 1,000 homes in Winterset

Top guest favourite
Apartment in Winterset
Luxury 2 Bed/2 Bath Condo-1 Block to Downtown
2 bedrooms, 2 beds, 2 private bathrooms
12–17 Sept
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4.98 out of 5 average rating, 40 reviews
Guest favourite
Home in Winterset
Rosehaven
3 bedrooms, 4 beds
24–29 Oct
4.98 out of 5 average rating, 133 reviews
Top guest favourite
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
2 bedrooms, 6 beds
21–26 Sept
4.99 out of 5 average rating, 123 reviews
Guest favourite
Home in Winterset
Charming abode
3 bedrooms, 3 beds
13–18 Sept
4.76 out of 5 average rating, 37 reviews
Top guest favourite
Home in Winterset
Debbie's Komfy Diggs Winter Set
2 bedrooms, 2 beds
13–18 Sept
4.97 out of 5 average rating, 348 reviews
Top guest favourite
Home in Winterset
The Little Brick House - Walkable to the Square
2 bedrooms, 2 beds
4–9 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Winterset
Winterset Square Loft/Retreat
1 bedroom, 1 bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Winterset
Covered Bridge Haven - 3BR House w/ Themed Rooms
3 bedrooms, 4 beds
16–21 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Winterset
​Cottage on Court: Historic Gem | 3 Blks to Square
2 bedrooms, 3 beds
1–6 Nov
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Flat in Winterset
The Suite Iowa Life
1 bedroom, 1 queen bed
9–14 Sept
4.94 out of 5 average rating, 418 reviews
Top guest favourite
Flat in Winterset
Luxury Studio- 1 Block to Town Square
1 queen bed
12–17 Sept
4.92 out of 5 average rating, 38 reviews
Top guest favourite
Home in Winterset
The Legacy Stone House
1 bedroom, 1 queen bed
12–17 Sept
4.95 out of 5 average rating, 341 reviews
Guest favourite
Farm stay in Winterset
Entire farmhouse in the country
4 bedrooms, 5 beds
17–22 Sept
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Home in Winterset
Hygge House in the ❤️ of historic Winterset
3 bedrooms, 4 beds
9–14 Sept
4.99 out of 5 average rating, 73 reviews
Top guest favourite
Home in Winterset
The Roost at Speckled Hen Farms.
4 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 100 reviews
Top guest favourite
Home in Winterset
The Little Red House
2 bedrooms, 4 beds
16–21 Sept
4.95 out of 5 average rating, 61 reviews
Top guest favourite
Guest suite in Winterset
2 BR fully furnished private condo sleeps 4
2 bedrooms, 2 queen beds
11–16 Sept
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
13–18 Sept
4.94 out of 5 average rating, 51 reviews
Flat in Winterset
Iowa Nice Winterset
3 bedrooms, 3 beds
11–16 Oct
4.85 out of 5 average rating, 442 reviews