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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.

Superhost
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
Superhost
Home in Winterset
The Legacy Stone House
The Legacy Stone House AirBnB is a historic residence located one mile east of Winterset, Iowa. Built in 1856 during the Settlement Era of Madison County, it is one of nearly 100 stone houses built during that time in the area. Officially named the William Anzi Nichols House, it is listed on the National Register of Historic Places. Convenient centralized location if visiting Madison County’s six covered bridges and two minutes from grocery, gas and dining.
$124 per night
Superhost
Apartment in Winterset
Winterset Wonderland
Located right off the main historic square in Winterset. The space is located in the old Madisonian building, built in 1906. This is a two bedroom, full kitchen apartment located above the Delirium Gallery. The space is also within a block away from the John Wayne Museum and the John Wayne Birth Place. It is also a prime location for the annual “Covered Bridge Festival” in the fall.
$168 per night

Other great vacation rentals in Madison County

Superhost
Home in Winterset
Rosehaven
$138 per night
Superhost
Cabin in Cumming
Iconic Iowa - A 1920 Built Country Cabin
$115 per night
Superhost
Home in Winterset
The Little Red House
$130 per night
Superhost
Cabin in Winterset
Whimsical cabin nestled in the woods
$135 per night
Superhost
Home in Winterset
The Roost at Speckled Hen Farms.
$199 per night
Superhost
Home in Winterset
The Home Place
$113 per night
Superhost
Home in Winterset
Hygge House in the ❤️ of historic Winterset
$180 per night
Superhost
Farm stay in Winterset
Historic Stone Farm House & Venue
$185 per night
Superhost
Farm stay in Winterset
Entire farmhouse in the country
$236 per night
Superhost
Guesthouse in Winterset
Luxury Guest Home in Beautiful Madison County
$247 per night
Superhost
Cabin in Winterset
Cabin on 10 Wooded Acres to Relax, Unwind & Gather
$500 per night
Apartment in Winterset
Iowa Nice Winterset
$87 per night

Destinations to explore

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