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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!

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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.

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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!

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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.

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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.

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The Holliwell House

You won't find another stay like this! *Peace, Quiet, and Privacy* This timeless farmhouse is uniquely nestled by iteself on a .66 mile private driveway and is only 5 minutes from the charming Winterset town square. No neighbors! You will see deer in your yard, hear songbirds chattering every morning, and see the most outstanding sunrises and sunsets. Enjoy a walk down the wildflower lined driveway, then take a left at the road, and you will see the famous Holliwell Covered Bridge.

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Historic Stone Farm House & Venue

Radiating charm, this civil war era home sits on six acres in scenic Madison County. With exposed stone walls, two working fireplaces, and a vine covering the house like a cozy blanket, you’ll see all the character of an old home, but relax in comfort with todays amenities. The property includes critters grazing in the pasture and the perfect barn for a country wedding, complete with string lights and church pews. Nestled 10 miles from Winterset and 40 minutes from Des Moines.

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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.

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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!

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The Roost at Speckled Hen Farms.

Explore the Iowa countryside with this 70's ranch as your relaxing base camp. Situated on 10 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!

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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.

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Whimsical cabin nestled in the woods

Iris Aisle is a whimsical, intimate venue + hemp farm located in Madison County Iowa. Our Victorian conservatory is used for many different events and classes and of course, plants. * please contact us first before booking. There can be events happening during your stay and/or there may be photographers on the property. We will make sure to let you know in advance if something is scheduled + during what times. This does not mean you have to leave the property.

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Cabin on 10 Wooded Acres to Relax, Unwind & Gather

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Iowa Nice Winterset

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Glamping Flower Farm Stay- PepperHarrow

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Remodeled Studio Apartment

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Charming Winterset Vacation Rental w/ Yard & Patio

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Close to metro-Camping Experience!

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Historic Judge Lewis House - Rickets Room

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The Suite Iowa Life

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