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19 homes

Home in Winterset
Debbie’s Komfy Diggs Winterset
2 beds
Dec 7 – 12
$90 per night
Superhost
Guesthouse in Winterset
Iowa Nice Winterset
3 beds
Dec 7 – 13
$72 per night
Superhost
Home in Winterset
The Legacy Stone House
1 queen bed
Dec 7 – 12
$124 per night, originally $140
Superhost
Cabin in Winterset
Whimsical cabin nestled in the woods
1 king bed
Dec 12 – 17
$135 per night
Superhost
Cabin in Saint Charles
NEW! St Charles 'Hilltop Mansion' w/ Mod Interior!
2 queen beds
Dec 18 – 23
$204 per night
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
6 beds
Dec 12 – 17
$175 per night
Superhost
Home in Winterset
Rosehaven
4 beds
Jan 1 – 6
$131 per night
Home in Winterset
The Bungalow in Winterset
5 beds
Dec 18 – 25
$204 per night
Superhost
Cabin in Winterset
Wooded Cabin on 10 Acres to Explore and Entertain
8 beds
Mar 10 – 16
$383 per night
Superhost
Condo in Winterset
2 BR fully furnished private condo
3 beds
Dec 7 – 13
$100 per night
Superhost
Home in Winterset
Hygge House in the ❤️ of historic Winterset
4 beds
Dec 12 – 17
$180 per night
Superhost
Cabin in Cumming
Iconic Iowa - A 1920 Built Country Cabin
5 beds
Dec 11 – 16
$125 per night
Superhost
Guest suite in Winterset
Entire Guest Home in Beautiful Madison County
6 beds
Jan 1 – 6
$200 per night
Apartment in Winterset
Wonderland Winter Set
2 beds
Dec 13 – 18
$195 per night
Home in Winterset
The Roost at Speckled Hen Farms.
4 beds
Jan 9 – 16
$159 per night, originally $199
Farm stay in Winterset
Entire farmhouse in the country
5 beds
Apr 16 – 21
$225 per night
Home in Earlham
Friendly Quarters
5 beds
Oct 1 – 6
$169 per night
Superhost
Tent in Winterset
A Boho GarlicTent Nestled in the Woods
1 bed
Dec 12 – 19
$130 per night
Superhost
Apartment in Winterset
The Suite Iowa Life
2 beds
Dec 7 – 12
$89 per night, originally $99
Superhost

One trip, two stays

Split your time between two places and discover more of Madison County.
Split your time between Winterset and Des Moines
$46 average per night
Two stays in Des Moines
$33 average per night