Holiday rentals in Winterset

Raccoon River Retreats

Come & experience the magic of this unique getaway,where the warmth of a renovated 1900's home meets the natural wonders of the Raccoon River. 30min from DSM,Ia.Whether you enjoy an adventure on the river of kayaking, paddle boarding, fishing,a peaceful moment along the biking trails,cozy up with a cup of coffee by the fireplace or a fire in the outdoor fire pit,our retreat has an idyllic setting to create lasting memories.A scenic landmark, local restaurant,Dairy shop & Dollar General are near

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.

Cabin w/ Hot Tub + Fire Pit + Private Trails

Looking for a place to slow down, reconnect, and make memories? Located 30 minutes from WDM and 90 minutes of Omaha, this modern cabin on a private wooded property is designed for couples, families, and small groups. Guests love: • Hot tub under the stars • Views from every room • Outdoor fire pit and fireplace • Fully stocked kitchen • River access and nature trails • Peaceful setting with easy access to small-town attractions Experience the ultimate retreat and choose your own adventure.

Charming Waterfront Tiny House & Sauna

The true definition of rest & relaxation, this unique tiny house is situated on a three-acre pond suitable for catch and release fishing, kayaking, or stand up paddle boarding. Bring your gear and leave your worries behind. Built with special touches and details including stained glass windows and intricate woodwork, this tiny home boasts warmth throughout. Wake up to bird songs and coffee with the sunrise. After a day of fun, take a soak in the wood-burning sauna and relax by the campfire.

Luxury Studio- 1 Block to Town Square

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.

Winterset Square Loft/Retreat

This apartment was created for you to relax, read, write, or create content. Located on the 2nd level of the historic Madisonian building in downtown Winterset. Walkable to coffee, restaurants and shopping. Drive-able to everything Madison County has to offer including the famous covered Bridges. You can pre-order charcuterie to have waiting in the fridge from tenant below (ask host for a link.) Coffee included (Keurig) during your stay or an adorable coffee shop is 3 doors down.

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!

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!

​Cottage on Court: Historic Gem | 3 Blks to 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

The 1894 by Doe A Deer | 2 br, 1 bath apartment

Welcome to The 1894 by Doe A Deer - a newly renovated 2 bedroom spacious apartment located in historic downtown Stuart! Enjoy restaurants, boutiques and coffee just steps from the front door. Relax and enjoy the view from your new favorite small town spot. Perfect for getting ready with your wedding party, families, girls trips, anniversaries & more! We can’t wait to host you!