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Vacation rentals in Madison County

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Top-rated vacation rentals in Madison County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cabin · Winterset
Whimsical cabin nestled in the woods
Iris Aisle is a whimsical, intimate venue + hemp farm located in Madison County Iowa. Our Victorian conservatory is used for many different events and classes and of course, plants. * please contact us first before booking. We host many events out here.
Dec 9 – 16
$135 per night
Home · Winterset
Debbie’s Komfy Diggs Winterset
Whole home, two bedroom, full kitchen, pet friendly and close to beautiful downtown historic Winterset. Home of John Wayne and the Bridges of Madison County. My name is Debbie, I have lived in Winterset for over fifty years. Can keep you informed of coming events and maps of the area. Located 13 miles from Interstate 35 and Interstate 80.
Feb 16 – 23
$77 per night
Apartment · Winterset
The Suite Iowa Life
Our acreage did not suffer any damage from the large Winterset Tornado on March 5, 2022. Praise God! This Suite is located on the main level of our home. It is not the entire house and does not include the upstairs space located above. There are no shared spaces and you will have your privacy. We are located just one mile outside of Winterset and 25 minutes from West Des Moines. We also run a small auto body and restoration business on the property but it should not interfere with your stay.
Dec 10 – 17
$98 per night

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Other great vacation rentals in Madison County

Condo · Winterset
2 BR fully furnished private condo
Mar 20 – 27
$101 per night
Cabin · Cumming
Iconic Iowa - A 1920 Built Country Cabin
May 26 – Jun 2
$146 per night
Guest suite · Winterset
Beautiful Country Retreat
Dec 7 – 14
$160 per night
Apartment · Winterset
Wonderland Winter Set
Aug 15 – 22
$158 per night
Home · Winterset
Hygge House in the ❤️ of historic Winterset
May 28 – Jun 4
$162 per night
Home · Winterset
The Roost at Speckled Hen Farms.
Jun 27 – Jul 4
$159 per night
Home · Winterset
The Bungalow in Winterset
Jan 24 – 31
$204 per night
Farm stay · Winterset
Entire farmhouse in the country
Jul 3 – 10
$151 per night
Home · Earlham
Friendly Quarters
Sep 3 – 10
$170 per night
Home · Winterset
Jul 5 – 12
$111 per night
Tent · Winterset
A Boho GarlicTent Nestled in the Woods
Nov 15 – 22
$130 per night
Guest suite · Saint Charles
Bridges of Madison County Adorable 2BR with pool!
May 17 – 24
$191 per night
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