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Search results; Over 1,000 homes in Winterset

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Flat in Winterset
Iowa Nice Winterset
3 bedrooms, 3 beds, 1 private bathroom
11–16 Oct
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4.85 out of 5 average rating, 442 reviews
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Top guest favourite
Home in Winterset
Rosehaven
3 bedrooms, 4 beds
24–29 Oct
4.98 out of 5 average rating, 134 reviews
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Top guest favourite
Home in Winterset
Debbie's Komfy Diggs Winter Set
2 bedrooms, 2 beds
20–25 Sept
4.97 out of 5 average rating, 350 reviews
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Top guest favourite
Flat in Winterset
The Suite Iowa Life
1 bedroom, 1 queen bed
20–25 Sept
4.94 out of 5 average rating, 421 reviews
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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, 17 reviews
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Top guest favourite
Home in Winterset
The Legacy Stone House
1 bedroom, 1 queen bed
1–6 Oct
4.95 out of 5 average rating, 346 reviews
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Home in Winterset
Charming abode
3 bedrooms, 3 beds
18–23 Sept
4.72 out of 5 average rating, 39 reviews
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Top guest favourite
Apartment in Winterset
Luxury 2 Bed/2 Bath Condo-1 Block to Downtown
2 bedrooms, 2 queen beds
18–23 Sept
4.98 out of 5 average rating, 41 reviews
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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, 31 reviews
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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, 124 reviews
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Top guest favourite
Flat in Winterset
Luxury Studio- 1 Block to Town Square
1 queen bed
18–23 Sept
4.92 out of 5 average rating, 38 reviews
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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
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Top guest favourite
Home in Winterset
Covered Bridge Haven - 3BR House w/ Themed Rooms
3 bedrooms, 4 beds
2–7 Nov
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Farm stay in Winterset
Entire farmhouse in the country
4 bedrooms, 5 beds
29 Oct – 3 Nov
4.98 out of 5 average rating, 62 reviews
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Top guest favourite
Home in Winterset
The Little Red House
2 bedrooms, 4 beds
29 Sept – 4 Oct
4.95 out of 5 average rating, 61 reviews
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Top guest favourite
Home in Winterset
Hygge House in the ❤️ of historic Winterset
3 bedrooms, 4 beds
19–24 Sept
4.99 out of 5 average rating, 74 reviews
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Top guest favourite
Tent in Winterset
Glamping Flower Farm Stay- PepperHarrow
1 king bed
20–25 Sept
4.98 out of 5 average rating, 55 reviews
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Top guest favourite
Home in Winterset
The Roost at Speckled Hen Farms.
4 bedrooms, 4 beds
18–23 Sept
5.0 out of 5 average rating, 100 reviews
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Guest favourite
Home in Winterset
Farm Escape | 12 Guest | Walk to Holliwell Bridge
5 bedrooms, 7 beds
20–25 Sept
4.94 out of 5 average rating, 52 reviews