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Search results; Over 1,000 homes in Winterset

Top guest favourite
Flat in Winterset
Winterset Square Loft/Retreat
1 bedroom, 1 bed
20–25 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Winterset
Rosehaven
3 bedrooms, 4 beds
28 Aug – 2 Sept
4.98 out of 5 average rating, 131 reviews
Top guest favourite
Flat in Winterset
Luxury Studio- 1 Block to Town Square
1 queen bed
20–25 Aug
4.95 out of 5 average rating, 37 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, 346 reviews
Top guest favourite
Home in Winterset
The Legacy Stone House
1 bedroom, 1 queen bed
4–9 Sept
4.95 out of 5 average rating, 334 reviews
Guest favourite
Home in Winterset
Charming abode
3 bedrooms, 4 beds
23–28 Aug
4.75 out of 5 average rating, 36 reviews
Top guest favourite
Flat in Winterset
The Suite Iowa Life
1 bedroom, 1 queen bed
25–30 Aug
4.93 out of 5 average rating, 410 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, 39 reviews
Top guest favourite
Home in Winterset
The Little Brick House - Walkable to the Square
2 bedrooms, 2 beds
4–9 Oct
5.0 out of 5 average rating, 27 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, 122 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, 26 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, 47 reviews
Top guest favourite
Home in Winterset
The Little Red House
2 bedrooms, 4 beds
20–25 Aug
4.95 out of 5 average rating, 60 reviews
Top guest favourite
Tent in Winterset
Glamping Flower Farm Stay- PepperHarrow
1 king bed
31 Aug – 5 Sept
4.98 out of 5 average rating, 53 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
Flat in Winterset
Iowa Nice Winterset
3 bedrooms, 3 beds
11–16 Oct
4.85 out of 5 average rating, 442 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, 73 reviews
Top guest favourite
Guest suite in Winterset
2 BR fully furnished private condo sleeps 4
2 bedrooms, 2 queen beds
20–25 Aug
4.87 out of 5 average rating, 134 reviews