filters

Search results; Over 1,000 homes in Winterset

Guest favourite
Farm stay in Winterset
Entire farmhouse in the country
4 bedrooms, 5 beds, 2 private bathrooms
17–22 Sept
,
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Winterset
The Suite Iowa Life
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 421 reviews
Top guest favourite
Home in Winterset
Debbie's Komfy Diggs Winter Set
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 350 reviews
Top guest favourite
Flat in Winterset
Winterset Square Loft/Retreat
1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Winterset
Rosehaven
3 bedrooms, 4 beds, 2 bathrooms
24–29 Oct
4.98 out of 5 average rating, 134 reviews
Top guest favourite
Apartment in Winterset
Luxury 2 Bed/2 Bath Condo-1 Block to Downtown
2 bedrooms, 2 queen beds, 2 bathrooms
14–19 Sept
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Home in Winterset
The Little Brick House - Walkable to the Square
2 bedrooms, 2 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Winterset
The Legacy Stone House
1 bedroom, 1 queen bed, 1 bathroom
14–19 Sept
4.95 out of 5 average rating, 345 reviews
Top guest favourite
Flat in Winterset
Luxury Studio- 1 Block to Town Square
1 queen bed, 1 bathroom
14–19 Sept
4.92 out of 5 average rating, 38 reviews
Home in Winterset
Charming abode
3 bedrooms, 3 beds, 1.5 bathrooms
14–19 Sept
4.72 out of 5 average rating, 39 reviews
Top guest favourite
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
2 bedrooms, 6 beds, 2 bathrooms
21–26 Sept
4.99 out of 5 average rating, 123 reviews
Guest favourite
Home in Saint Charles
Historic 1909 Farmhouse in Madison County
3 bedrooms, 4 beds, 1.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Van Meter
New Build w/ Fab design! Theater/Game Sleeps 12!
4 bedrooms, 7 beds, 3 bathrooms
14–19 Sept
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Home in Winterset
Covered Bridge Haven - 3BR House w/ Themed Rooms
3 bedrooms, 4 beds, 3 bathrooms
2–7 Nov
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Winterset
Hygge House in the ❤️ of historic Winterset
3 bedrooms, 4 beds, 1 bathroom
15–20 Sept
4.99 out of 5 average rating, 74 reviews
Top guest favourite
Home in Winterset
​Cottage on Court: Historic Gem | 3 Blks to Square
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Nov
5.0 out of 5 average rating, 48 reviews
Rooms in Winterset
Blue Hill Bed and Breakfast
2 bedrooms, 3 beds, 1 bathroom
20–25 Oct
Superhost
Home in New Virginia
Spacious farmhouse beautifully decorated
4 bedrooms, 9 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Norwalk
Victoria's House at Rose Farm
3 bedrooms, 6 beds, 2 bathrooms
1–6 Nov
4.95 out of 5 average rating, 98 reviews