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.

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