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.

Clanton Creek ‘Cabin’

Clanton Creek ‘Cabin’ is a quiet and rustic stay. If you are looking for a way to get away from the city life and enjoy being out in nature, this cabin is for you! We are surrounded by beautiful timbered ridges, native grass fields, and the relaxing Clanton creek. Located in the heart of some of Iowa’s best deer hunting, this cabin is set up with the hunter in mind! Our cabin is in the center of nearly 3,000 acres of public hunting land. We are also a short drive from some great fishing lakes!

The Suite Iowa Life

THE BEST VALUE IN WINTERSET 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 where we live and work. It is a PRIVATE, FULLY EQUIPPED APARTMENT, UNSHARED SPACE. Separate entrance. Pets allowed. Access to yard and beautiful country views. * NEW MATTRESS * November 2023 Large backyard, grill, fire pit, close to town & centrally located amongst the six bridges. PLEASE READ FULL DESCRIPTION.

Hygge House in the ❤️ of historic Winterset

Hygge: a Norwegian word for a mood of coziness, and comfortable conviviality with feelings of wellness and contentment. Swing on the quaint side porch or congregate on the large back deck. Gather at the harvest table in the front room. Cook a meal in the kitchen. Walk the 3 blocks to the historic square and enjoy shops, restaurants, museums and parks or take a bike ride. Bring your girlfriends for a craft weekend or your family and enjoy all our wonderful town has to offer!

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.

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.