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Search results; Over 1,000 homes in Winterset

Top guest favourite
Home in Winterset
The Legacy Stone House
1 bedroom, 1 bed, 1 private bathroom
30 Aug – 4 Sept
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4.95 out of 5 average rating, 334 reviews
Guest favourite
Home in Winterset
Rosehaven
3 bedrooms, 4 beds
28 Aug – 2 Sept
4.98 out of 5 average rating, 130 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, 13 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, 344 reviews
Guest favourite
Home in Winterset
Charming abode
3 bedrooms, 4 beds
9–14 Aug
4.74 out of 5 average rating, 31 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
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
2 bedrooms, 6 beds
1–6 Sept
4.99 out of 5 average rating, 120 reviews
Top guest favourite
Flat in Winterset
Luxury Studio- 1 Block to Town Square
1 queen bed
17–22 Aug
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Home in Winterset
The Little Brick House - Walkable to the Square
2 bedrooms, 2 beds
20–25 Aug
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Winterset
The Suite Iowa Life
1 bedroom, 1 queen bed
14–19 Aug
4.94 out of 5 average rating, 409 reviews
Top guest favourite
Home in Winterset
The Little Red House
2 bedrooms, 4 beds
19–24 Aug
4.97 out of 5 average rating, 58 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
Covered Bridge Haven - 3BR House w/ Themed Rooms
3 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Winterset
Hygge House in the ❤️ of historic Winterset
3 bedrooms, 4 beds
25–30 Aug
4.99 out of 5 average rating, 71 reviews
Top guest favourite
Home in Winterset
​Cottage on Court: Historic Gem | 3 Blks to Square
2 bedrooms, 3 beds
24–29 Aug
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Home in Winterset
The Roost at Speckled Hen Farms.
4 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 100 reviews
Guest favourite
Home in Winterset
Farm Escape | 12 Guest | Walk to Holliwell Bridge
5 bedrooms, 7 beds
23–28 Aug
4.94 out of 5 average rating, 49 reviews
Top guest favourite
Tent in Winterset
Glamping Flower Farm Stay- PepperHarrow
1 king bed
11–16 Aug
4.98 out of 5 average rating, 52 reviews
Flat in Winterset
Iowa Nice Winterset
3 bedrooms, 3 beds
26–31 Aug
4.85 out of 5 average rating, 441 reviews