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512 homes

Home in Winterset
The Legacy Stone House
1 queen bed
Oct 24 – 30
$120 per night, originally $140
Superhost
Home in Winterset
Debbie’s Komfy Diggs Winterset
2 beds
Oct 30 – Nov 4
$85 per night
Superhost
Condo in Winterset
2 BR fully furnished private condo
3 beds
Oct 16 – 21
$100 per night
Superhost
Guesthouse in Winterset
Iowa Nice Winterset
3 beds
Oct 31 – Nov 5
$70 per night
Superhost
Home in Winterset
Hygge House in the ❤️ of historic Winterset
4 beds
Oct 30 – Nov 5
$180 per night
Superhost
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
6 beds
Oct 24 – 29
$175 per night
Superhost
Apartment in Winterset
Wonderland Winter Set
2 beds
Oct 21 – 26
$195 per night
Cabin in Winterset
Whimsical cabin nestled in the woods
1 king bed
Nov 14 – 19
$137 per night
Superhost
Guest suite in Winterset
Beautiful Country Retreat
6 beds
Oct 24 – 29
$200 per night
Home in Winterset
Rosehaven
4 beds
Oct 9 – 14
$131 per night
Home in Winterset
The Bungalow in Winterset
5 beds
Oct 24 – 29
$201 per night
Superhost
Home in Winterset
The Roost at Speckled Hen Farms.
4 beds
Oct 31 – Nov 5
$199 per night
Farm stay in Winterset
Entire farmhouse in the country
5 beds
Oct 30 – Nov 4
$225 per night
Cabin in Cumming
Iconic Iowa - A 1920 Built Country Cabin
5 beds
Oct 9 – 14
$125 per night
Superhost
Guest suite in Saint Charles
Bridges of Madison County Adorable 2BR with pool!
2 beds
Oct 6 – 11
$225 per night
Tent in Winterset
A Boho GarlicTent Nestled in the Woods
1 bed
Oct 23 – 28
$130 per night
Superhost
Apartment in Des Moines
Stylish 1 Bed Apt w/ Free Parking Near Drake
1 queen bed
Oct 10 – 15
$43 per night, originally $51
Farm stay in Indianola
Cottage getaway; perfect for some relaxation
2 beds
Oct 9 – 14
$129 per night
Superhost
Home in Earlham
Hidden Timber-away from the noise and chaos.
4 beds
Mar 8 – 13
$200 per night
Townhouse in Des Moines
Cozy retreat near Downtown & Drake University!
1 queen bed
Oct 9 – 14
$46 per night, originally $78