Holiday rentals in Madison County

Rosehaven

Enjoy the nostalgic small town charm of Winterset, Iowa while staying at Rosehaven, within walking distance to the town square. Between the historic Madison County covered bridges in the area, the John Wayne museum and his preserved birthplace, as well as the numerous wineries and local events - Winterset is full of reasons to visit and stay at Rosehaven - a short 30 min. drive to Des Moines. Rosehaven is easy to find, with plenty of room for up to 5 or 6 guests. We look forward to having you!

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.

Luxury Private Space, close to West DM!

Step into our luxurious studio that seamlessly blends style and functionality. This elegant space greets you with the warm glow of a modern fireplace, perfect for cozy evenings after a day of exploration in the quaint town square located just a block away. The studio's clever design boasts a well-equipped workstation, the sleek and space-saving Murphy bed transforms the room from a productive workspace by day to a tranquil sleeping area by night. The promise of an exquisite stay awaits you.

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.

Iconic Iowa - A 1920 Built Country Cabin

This 1920 Log Cabin sits at the beginning of the Madison County covered bridges Scenic Byway and features 2 rural country acres of space and a wonderfully remodeled home with loads of character and style. Situated just 10 minutes south of the West Glen area of West Des Moines and 25 minutes from downtown Des Moines, you'll experience the quiet and beauty of rural Iowa while being close enough for shopping or to go out for a nice dinner or evening show. This is a great getaway.

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.

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.

The Roost at Speckled Hen Farms.

Explore the Iowa countryside with this 70's ranch as your relaxing base camp. Situated on 5 acres of rolling hills in rural Madison County, Iowa, this centrally located homestead has something for every kind of traveler. The charming town of Winterset is just minutes away, as well the historic Covered Bridges, wineries, breweries, parks and more. Located next to Speckled Hen Farms farm store and Lone Oaks Farm, you can take in an occasional music event or class!

Renovated Cottage: 3 blocks to shops on square

Our renovated 1910 "Cottage on Court" is more than just a place to stay; it’s a home where memories are made. This charming 2-bedroom, 1.5-bath cottage blends historic charm with modern amenities for a perfect stay. Nestled just 3 blocks from the downtown square, you’re close to shops, cafes, and attractions like the John Wayne Birthplace and Quilt Museum. Book your stay today and discover the allure of our charming cottage in the heart of historic Winterset, IA

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.