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Search results; Over 1,000 homes in Winterset

Top guest favourite
Flat in Winterset
The Suite Iowa Life
1 bedroom, 1 bed, 1 private bathroom
14–19 Aug
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4.94 out of 5 average rating, 406 reviews
Top guest favourite
Home in Winterset
Debbie's Komfy Diggs Winter Set
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 343 reviews
Top guest favourite
Flat in Winterset
Luxury Studio- 1 Block to Town Square
1 queen bed, 1 bathroom
17–22 Aug
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Home in Winterset
The Legacy Stone House
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.95 out of 5 average rating, 334 reviews
Top guest favourite
Flat in Winterset
Winterset Square Loft/Retreat
1 bedroom, 1 bed, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Apartment in Winterset
Luxury 2 Bed/2 Bath Condo-1 Block to Downtown
2 bedrooms, 2 queen beds, 2 bathrooms
24–29 Aug
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Home in Winterset
The Little Red House
2 bedrooms, 4 beds, 1 bathroom
5–10 Aug
4.97 out of 5 average rating, 58 reviews
Guest favourite
Home in Winterset
Rosehaven
3 bedrooms, 4 beds, 2 bathrooms
28 Aug – 2 Sept
4.98 out of 5 average rating, 129 reviews
Top guest favourite
Home in Winterset
The Little Brick House - Walkable to the Square
2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Tent in Winterset
Glamping Flower Farm Stay- PepperHarrow
1 king bed, WC
6–11 Aug
5.0 out of 5 average rating, 51 reviews
Flat in Winterset
Iowa Nice Winterset
3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.85 out of 5 average rating, 441 reviews
Guest favourite
Home in Winterset
Charming abode
3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
4.76 out of 5 average rating, 29 reviews
Top guest favourite
Guest suite in Winterset
2 BR fully furnished private condo sleeps 4
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Aug
4.87 out of 5 average rating, 134 reviews
Top guest favourite
Home in Winterset
​Cottage on Court: Historic Gem | 3 Blks to Square
2 bedrooms, 3 beds, 1.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Winterset
Hygge House in the ❤️ of historic Winterset
3 bedrooms, 4 beds, 1 bathroom
18–23 Aug
4.99 out of 5 average rating, 70 reviews
Top guest favourite
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
2 bedrooms, 6 beds, 2 bathrooms
1–6 Sept
4.99 out of 5 average rating, 119 reviews
Top guest favourite
Home in Winterset
Covered Bridge Haven - 3BR House w/ Themed Rooms
3 bedrooms, 4 beds, 3 bathrooms
11–16 Aug
5.0 out of 5 average rating, 24 reviews
Rooms in Winterset
Blue Hill Bed and Breakfast
2 bedrooms, 3 beds, 1 bathroom
20–25 Oct
Home in Saint Charles
Historic 1909 Farmhouse Near Iowa State Fair
3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews