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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
8–13 Aug
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4.95 out of 5 average rating, 331 reviews
Guest favourite
Home in Winterset
Rosehaven
4.98 out of 5 average rating, 129 reviews, 3 bedrooms, 4 beds, 2 bathrooms
28 Aug – 2 Sept
Top guest favourite
Flat in Winterset
Luxury Studio- 1 Block to Town Square
4.94 out of 5 average rating, 33 reviews, 1 bed, 1 bathroom
17–22 Aug
Top guest favourite
Home in Winterset
Debbie's Komfy Diggs Winter Set
4.97 out of 5 average rating, 340 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Home in Winterset
The Little Brick House - Walkable to the Square
5.0 out of 5 average rating, 24 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
7–12 Sept
Top guest favourite
Flat in Winterset
The Suite Iowa Life
4.94 out of 5 average rating, 403 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Aug
Top guest favourite
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
4.99 out of 5 average rating, 117 reviews, 2 bedrooms, 6 beds, 2 bathrooms
29 Aug – 3 Sept
Top guest favourite
Flat in Winterset
Winterset Square Loft/Retreat
5.0 out of 5 average rating, 10 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Aug
Top guest favourite
Apartment in Winterset
Luxury 2 Bed/2 Bath Condo-1 Block to 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 Red House
4.96 out of 5 average rating, 57 reviews, 2 bedrooms, 4 beds, 1 bathroom
5–10 Aug
Guest favourite
Home in Winterset
Charming abode
4.75 out of 5 average rating, 28 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
Top guest favourite
Home in Winterset
Hygge House in the ❤️ of historic Winterset
4.99 out of 5 average rating, 69 reviews, 3 bedrooms, 4 beds, 1 bathroom
18–23 Aug
Top guest favourite
Home in Winterset
Covered Bridge Haven - 3BR House w/ Themed Rooms
5.0 out of 5 average rating, 24 reviews, 3 bedrooms, 4 beds, 3 bathrooms
11–16 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
24–29 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
5–10 Aug
Guest favourite
Home in Winterset
Farm Escape | 12 Guest | Walk to Holliwell Bridge
4.94 out of 5 average rating, 49 reviews, 5 bedrooms, 7 beds, 2.5 bathrooms
8–13 Aug
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
Flat in Winterset
Iowa Nice Winterset
4.85 out of 5 average rating, 441 reviews, 3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Winterset
The Roost at Speckled Hen Farms.
5.0 out of 5 average rating, 98 reviews, 4 bedrooms, 4 beds, 2 bathrooms
16–21 Aug