Holiday houses in Madison County

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.

The Legacy Stone House

The most unique stay in Winterset! 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.

The Home Place

The Home Place, built in 1895, sits three blocks from the Winterset square. It showcases local businesses and Winterset history while offering modern amenities and the comforts of home. Soaps and cleaning supplies are as fragrant free as possible, allowing for a near hypoallergenic haven. No pets for this reason. We offer a king bed, a queen bed, a dedicated office, and a handicapped entrance ramp. Cots, Pack-N-Play, and baby gates are available upon request. Welcome to The Home Place.

Iowa Nice Winterset

You are renting a piece of “Iowa Nice”, please read my reviews, the entire Lower level but must pass through my area to go down stairs. I greet every guest so it is IMPORTANT to let me know your arrival time. IowaNice is a real thing not just a saying. I will be happy to cook Iowa home style meals for you, just let me know ahead of time. Also available for child care and dog sitting. Long term guest can have laundry done. I want you to know what small town Iowa is like.

Glamping Flower Farm Stay- PepperHarrow

Escape to the beauty and tranquility of PepperHarrow, a 20 acre flower farm in Madison County. Our glamping tent offers a unique and peaceful getaway, surrounded by 8.5 acres of stunning flowers. Relax and unwind amongst 2.5 acres of lavender, 1.5 acres of annuals, 1 acre of perennials, and wildflower areas supporting local pollinators. Experience the magic of nature from the comfort of our cozy glamping tent, perched atop the bluffs overlooking the Middle River Valley.

Friendly Quarters

This charming location is a farmhouse style home built in 1914. Easily found on the main street through town, a one block walk in any given direction will put you at the center of the city. A grocery story, eating establishments, gift shops and community center are conveniently located in the downtown area. Friendly Quarters operates as a non-profit organization to support the missions and ministries of Earlham Friends (Quaker) Church located right next door.

Entire farmhouse in the country

Just 10 minutes north of Winterset, stay in a Covered Bridge House. You’ll love visiting the historic bridges & John Wayne Birthplace Museum. Perfect for families and groups, enjoy relaxing at our newly renovated “modern farmhouse style” home. A quiet retreat, nestled in beautiful rolling hills. Built by Eli Cox family, renowned covered bridge builders. It’s a short 5 minute drive to local attractions: Winterset Cidery, Covered Bridges Winery & Guye Woods.

Whimsical cabin nestled in the woods

Iris Aisle is a whimsical, intimate venue + hemp farm in Madison County, Iowa. Our Victorian conservatory hosts events, classes, and of course—plants. ✨ Now offering elopement add-ons for couples seeking a dreamy, intimate setting. Please contact us before booking—events or photographers may be onsite. We’ll notify you of any scheduled activity + times, but you are always welcome to enjoy the space. For non-Airbnb stays, visit our website.

Covered Bridge Haven - 3BR House w/ Themed Rooms

Charming 3-bed, 3-bath home on Winterset's north side, just 1.2 miles from the town square and Madison County Courthouse. Only 2 miles from Cutler-Donahoe Covered Bridge and City Park. Enjoy a Madison County-themed master bedroom and an Iowa State Fair-themed bedroom. Perfect for families or groups seeking a cozy, themed retreat with easy access to Winterset’s historic charm and attractions. Relax in comfort and explore the heart of Iowa!