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Vacation rentals in Madison County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Madison County

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

Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
This elevated second story apartment has an incredible view of the historic downtown square and courthouse. Bring your group to be in a centralized location near dining/bars , shopping, museums, and a movie theatre. Accommodations for a group of seven is ideal for getaways or special occasions. The unique relief art sculpture of a tree and eagles will captivate you. A full kitchen with all the essentials. 6 beds and spacious 3/4 bath and a second 3/4 bath opened for 5 or more guests.
$175 per night
Rental unit in Winterset
The Suite Iowa Life
Don’t spend your money on an impersonal hotel when you can stay at our “home away from home!” This Suite is located on the main level of our home. It is a PRIVATE, FULLY EQUIPPED APARTMENT, UNSHARED SPACE. Separate entrance. Pets allowed. Access to yard and beautiful country views. This is THE BEST VALUE in the Winterset area. Large backyard, grill, fire pit, close to the John Wayne Birth Place & Museum and centrally located amongst Bridges of Madison County. PLEASE READ FULL DESCRIPTION.
$91 per night
Cabin in 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. There can be events happening during your stay and/or there may be photographers on the property. We will make sure to let you know in advance if something is scheduled + during what times. This does not mean you have to leave the property.
$135 per night

Other great vacation rentals in Madison County

Home in Winterset
Hygge House in the ❤️ of historic Winterset
$180 per night
Home in Winterset
$146 per night
Cabin in Cumming
Iconic Iowa - A 1920 Built Country Cabin
$122 per night
Condo in Winterset
2 BR fully furnished private condo
$102 per night
Home in Winterset
The Roost at Speckled Hen Farms.
$199 per night
Guest suite in Winterset
Luxury Guest Home in Beautiful Madison County
$239 per night
Rental unit in Winterset
Iowa Nice Winterset
$71 per night
Home in Winterset
The Bungalow in Winterset
$204 per night
Rental unit in Winterset
Wonderland Winter Set
$139 per night
Home in Winterset
Cheerful, 2 bedroom home in a quiet neighborhood.
$126 per night
Cabin in Winterset
Cabin on 10 Wooded Acres to Relax, Unwind & Gather
$382 per night
Farm stay in Winterset
Entire farmhouse in the country
$215 per night

Other types of stays on Airbnb

  1. Airbnb
  2. United States
  3. Iowa
  4. Madison County