Winterset, IA 50273, USA Vacation rentals • comparison for Airbnb, Vrbo and Booking prices

United States Iowa Winterset vacation rental compare prices direct by owner 33964924

Charming Winterset Vacation Rental w/ Yard & Patio

5.0 (34)

4 Bedrooms • 8 Guests

$258 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 24921598

The Roost at Speckled Hen Farms.

5.0 (113)

4 Bedrooms • 8 Guests

$296 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 33554518

Cottage on Court: Historic Gem | 3 Blks to Square

5.0 (58)

2 Bedrooms • 6 Guests

$217 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 13061891

Cabin on 10 Wooded Acres to Relax, Unwind & Gather

5.0 (78)

5 Bedrooms • 12 Guests

$694 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 26625075

Entire farmhouse in the country

5.0 (86)

4 Bedrooms • 8 Guests

$456 avg/night

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United States Iowa Winterset vacation rental compare prices direct by owner 9523235

Aerie Loft Apartment with view that sleeps 7

5.0 (105)

2 Bedrooms • 7 Guests

$243 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 29287664

The Home Place

5.0 (49)

2 Bedrooms • 6 Guests

$184 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 33375361

Holliwell Bridge Retreat - Private, Spacious & Close to town! Great for Groups!

5.0 (19)

5 Bedrooms • 12 Guests

Available on

United States Iowa Winterset vacation rental compare prices direct by owner 33833186

Historic Judge Lewis House - Judge Lewis Room

5.0 (6)

3 Bedrooms • 2 Guests

$185 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 34827349

Charming Winterset Vacation Rental w/ Yard & Patio

5.0 (37)

4 Bedrooms • 8 Guests

Available on

United States Iowa Winterset vacation rental compare prices direct by owner 37484305

Luxury 2 Bed/2 Bath Condo-1 Block to Downtown

5.0 (28)

2 Bedrooms • 5 Guests

$164 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 39401519

Covered Bridge Haven - 3BR House w/ Themed Rooms

5.0 (19)

3 Bedrooms • 10 Guests

$274 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 40163842

The Little Brick House - Walkable to the Square

5.0 (13)

2 Bedrooms • 4 Guests

$182 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 40413957

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

5.0 (5)

3 Bedrooms • 10 Guests

Available on

United States Iowa Winterset vacation rental compare prices direct by owner 40617588

Charming abode

5.0 (2)

3 Bedrooms • 8 Guests

$179 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 40662729

The Little Brick House - Walkable to the Square Dining & Shopping

5.0 (6)

2 Bedrooms • 4 Guests

Available on

United States Iowa Winterset vacation rental compare prices direct by owner 15719039

Hygge House in the ❤️ of historic Winterset

5.0 (66)

3 Bedrooms • 8 Guests

$246 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 24522010

Rosehaven

5.0 (112)

3 Bedrooms • 6 Guests

$202 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 8268379

Debbie's Komfy Diggs Winter Set

5.0 (313)

2 Bedrooms • 4 Guests

$137 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 5911530

The Legacy Stone House

2 Bedrooms • 6 Guests

$185 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 27362071

Farm Escape | 12 Guest | Walk to Holliwell Bridge

5.0 (43)

5 Bedrooms • 12 Guests

Luxury Studio- 1 Block to Town Square

4.9 (21)

1 Bedroom • 3 Guests

$124 avg/night

United States Iowa Winterset vacation rental compare prices direct by owner 9854935

Whimsical cabin nestled in the woods

4.9 (77)

1 Bedroom • 3 Guests

$170 avg/night

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