Search results; Over 1,000 homes in Winterset

Top guest favourite
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
2 bedrooms, 6 beds, 2 private bathrooms
26–31 Jul
,
5.0 out of 5 average rating, 114 reviews
Guest favourite
Home in Winterset
Rosehaven
4 beds
19–24 Aug
4.98 out of 5 average rating, 123 reviews
Top guest favourite
Flat in Winterset
Luxury Studio- 1 Block to Town Square
1 queen bed
20–25 Jul
4.94 out of 5 average rating, 31 reviews
Guest favourite
Home in Winterset
The Legacy Stone House
1 queen bed
18–23 Jul
4.95 out of 5 average rating, 329 reviews
Top guest favourite
Home in Winterset
Debbie's Komfy Diggs Winter Set
2 beds
27 Aug – 1 Sept
4.97 out of 5 average rating, 338 reviews
Guest favourite
Home in Winterset
Charming abode
4 beds
9–14 Aug
4.72 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Winterset
The Suite Iowa Life
1 queen bed
14–19 Aug
4.94 out of 5 average rating, 401 reviews
Top guest favourite
Home in Winterset
The Little Red House
4 beds
5–10 Aug
4.96 out of 5 average rating, 57 reviews
Top guest favourite
Apartment in Winterset
Luxury 2 Bed/2 Bath Condo-1 Block to Downtown
2 queen beds
24–29 Aug
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Flat in Winterset
Winterset Square Loft/Retreat
1 bed
19–24 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Winterset
The Roost at Speckled Hen Farms.
4 beds
19–24 Jul
5.0 out of 5 average rating, 97 reviews
Top guest favourite
Home in Winterset
The Little Brick House - Walkable to the Square
2 beds
7–12 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Winterset
Hygge House in the ❤️ of historic Winterset
4 beds
11–16 Aug
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Home in Winterset
​Cottage on Court: Historic Gem | 3 Blks to Square
3 beds
17–22 Aug
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Farm stay in Winterset
Entire farmhouse in the country
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
4 beds
3–8 Aug
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Winterset
Charming Winterset Vacation Rental w/ Yard & Patio
5 beds
16–21 Aug
4.97 out of 5 average rating, 39 reviews
Guest favourite
Home in Winterset
Farm Escape | 12 Guest | Walk to Holliwell Bridge
7 beds
8–13 Aug
4.94 out of 5 average rating, 48 reviews
Top guest favourite
Tent in Winterset
Glamping Flower Farm Stay- PepperHarrow
1 king bed
22–27 Jul
5.0 out of 5 average rating, 50 reviews