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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
Top guest favourite
Flat in Winterset
Luxury Studio- 1 Block to Town Square
4.94 out of 5 average rating, 31 reviews, 1 bed, 1 bathroom
11–16 Jul
Guest favourite
Home in Winterset
Rosehaven
4.98 out of 5 average rating, 122 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
Top guest favourite
Home in Winterset
Debbie's Komfy Diggs Winter Set
4.97 out of 5 average rating, 335 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Flat in Winterset
The Suite Iowa Life
4.94 out of 5 average rating, 401 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
5.0 out of 5 average rating, 114 reviews, 2 bedrooms, 6 beds, 2 bathrooms
29 Aug – 3 Sept
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 Brick House - Walkable to the Square
5.0 out of 5 average rating, 22 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
7–12 Sept
Top guest favourite
Home in Winterset
The Roost at Speckled Hen Farms.
5.0 out of 5 average rating, 96 reviews, 4 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Flat in Winterset
Winterset Square Loft/Retreat
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Aug
Guest favourite
Home in Winterset
Charming abode
4.72 out of 5 average rating, 25 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
13–18 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
17–22 Jul
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
18–23 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
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
Tent in Winterset
Glamping Flower Farm Stay- PepperHarrow
5.0 out of 5 average rating, 50 reviews, 1 bed, Toilet with sink
22–27 Jul
Guest favourite
Home in Winterset
Charming Winterset Vacation Rental w/ Yard & Patio
4.97 out of 5 average rating, 38 reviews, 4 bedrooms, 5 beds, 1.5 bathrooms
16–21 Aug
Guest favourite
Cabin in Winterset
Historic Stone Farm Inn & Venue
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 6 beds, 1 bathroom
12–17 Jul
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
10–15 Aug