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Search results; Over 1,000 homes in Winterset

Descriptions are based on details hosts provide
Guest favourite
Home in Winterset
The Legacy Stone House
1 bedroom, 1 bed, 1 private bathroom
18–23 Jul
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4.95 out of 5 average rating, 329 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, 9 reviews
Guest favourite
Home in Winterset
Walk to the square, near covered bridges
3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
4.98 out of 5 average rating, 124 reviews
Guest favourite
Home in Winterset
Charming abode
3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
4.72 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Winterset
Luxury Studio- 1 Block to Town Square
1 queen bed, 1 bathroom
20–25 Jul
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
2 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 115 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, 338 reviews
Top guest favourite
Apartment in Winterset
Fireplace and a balcony, near 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
4 blocks from the square in Winterset
2 bedrooms, 2 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Winterset
Country views, fire pit, and a grill
1 bedroom, 1 queen bed, 1 bathroom
14–19 Aug
4.94 out of 5 average rating, 401 reviews
Top guest favourite
Home in Winterset
A 70s ranch on 5 rolling acres
4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 97 reviews
Top guest favourite
Home in Winterset
The Little Red House
2 bedrooms, 4 beds, 1 bathroom
5–10 Aug
4.96 out of 5 average rating, 57 reviews
Top guest favourite
Home in Winterset
​Cottage on Court: Historic Gem | 3 Blks to Square
2 bedrooms, 3 beds, 1.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Winterset
Bikes and a backyard, 3 blocks from square
3 bedrooms, 4 beds, 1 bathroom
11–16 Aug
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Home in Winterset
Themed rooms near the covered bridges
3 bedrooms, 4 beds, 3 bathrooms
3–8 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Farm stay in Winterset
Entire farmhouse in the country
4 bedrooms, 5 beds, 2 bathrooms
20–25 Aug
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Guest suite in Winterset
2 blocks from courthouse square, free parking
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Jul
4.87 out of 5 average rating, 134 reviews
Top guest favourite
Tent in Winterset
Glamping on a flower farm’s bluffs
1 king bed, WC
22–27 Jul
5.0 out of 5 average rating, 50 reviews
Guest favourite
Home in Winterset
Charming Winterset Vacation Rental w/ Yard & Patio
4 bedrooms, 5 beds, 1.5 bathrooms
16–21 Aug
4.97 out of 5 average rating, 39 reviews