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Search results; Over 1,000 homes in Winterset

Guest favourite

Home in Winterset

The Legacy Stone House

1 bedroom, 1 bed, 1 private bathroom

18–23 Jul

$953 SGD for 5 nights

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4.95 out of 5 average rating, 329 reviews

Top guest favourite

Flat in Winterset

Luxury Studio- 1 Block to Town Square

1 queen bed

20–25 Jul

$805 SGD for 5 nights

4.94 out of 5 average rating, 31 reviews

Top guest favourite

Home in Winterset

Debbie's Komfy Diggs Winter Set

2 bedrooms, 2 beds

27 Aug – 1 Sept

$732 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 336 reviews

Guest favourite

Home in Winterset

Rosehaven

3 bedrooms, 4 beds

19–24 Aug

$1,198 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 123 reviews

Top guest favourite

Flat in Winterset

The Suite Iowa Life

1 bedroom, 1 queen bed

13–18 Aug

$673 SGD for 5 nights

4.94 out of 5 average rating, 401 reviews

Top guest favourite

Loft in Winterset

Aerie Loft Apartment with view that sleeps 7

2 bedrooms, 6 beds

29 Aug – 3 Sept

$1,410 SGD for 5 nights

5.0 out of 5 average rating, 114 reviews

Guest favourite

Home in Winterset

Charming abode

3 bedrooms, 4 beds

13–18 Jul

Free cancellation

4.72 out of 5 average rating, 25 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

$903 SGD for 5 nights

4.97 out of 5 average rating, 35 reviews

Top guest favourite

Home in Winterset

The Little Red House

2 bedrooms, 4 beds

17–22 Jul

$1,105 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 57 reviews

Top guest favourite

Home in Winterset

The Roost at Speckled Hen Farms.

4 bedrooms, 4 beds

19–24 Jul

$1,809 SGD for 5 nights

5.0 out of 5 average rating, 97 reviews

Top guest favourite

Flat in Winterset

Winterset Square Loft/Retreat

1 bedroom, 1 bed

19–24 Aug

$922 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Top guest favourite

Home in Winterset

The Little Brick House - Walkable to the Square

2 bedrooms, 2 beds

7–12 Sept

$1,041 SGD for 5 nights

5.0 out of 5 average rating, 23 reviews

Top guest favourite

Home in Winterset

Cottage on Court: Historic Gem | 3 Blks to Square

2 bedrooms, 3 beds

17–22 Aug

$1,319 SGD for 5 nights

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

11–16 Aug

$1,412 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 68 reviews

Guest favourite

Home in Winterset

Farm Escape | 12 Guest | Walk to Holliwell Bridge

5 bedrooms, 7 beds

8–13 Aug

$2,848 SGD for 5 nights

4.94 out of 5 average rating, 48 reviews

Guest favourite

Home in Winterset

Charming Winterset Vacation Rental w/ Yard & Patio

4 bedrooms, 5 beds

16–21 Aug

$1,452 SGD for 5 nights

4.97 out of 5 average rating, 39 reviews

Top guest favourite

Farm stay in Winterset

Entire farmhouse in the country

4 bedrooms, 5 beds

20–25 Aug

$2,621 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 62 reviews

Top guest favourite

Home in Winterset

Covered Bridge Haven - 3BR House w/ Themed Rooms

3 bedrooms, 4 beds

3–8 Aug

$2,453 SGD for 5 nights

5.0 out of 5 average rating, 24 reviews

Top guest favourite

Tent in Winterset

Glamping Flower Farm Stay- PepperHarrow

1 king bed

22–27 Jul

$873 SGD for 5 nights

5.0 out of 5 average rating, 50 reviews