Holiday houses in Winterset

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.

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.

Effortless Landing near Airport

Welcome to the Effortless Landing! Our super clean and comfy, Boho style retreat. Private keyless entry with off street parking. Enjoy a queen bed, additional pull out queen bed in couch, local coffee, & all the amenities like fiber wifi, TV, linens, full kitchen, & laundry. Add that to the wonderful surroundings of the city of Des Moines, in a quiet, centrally located neighborhood. Conveniently located 4 minutes from the Des Moines International Airport, & 7 minutes to Downtown Des Moines!

“The Miles Barn” Gorgeous Industrial Loft

Welcome to our beautiful open concept industrial loft. Upon entering our cozy abode, you'll find a clean, bright, well decorated home with many great amenities where you can kick back, relax and enjoy your stay. If high ceilings and beautiful polished concrete floors are your thing, you will be in heaven. Steel railings give it a true industrial feel. Everything needed for your stay is well thought out and ready to be used. We hope you love our loft as much as we do! ***Pet Fee is $125***

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.

Peaceful Setting & Modern Style

Escape the hustle and bustle of the city and retreat to your own private oasis with this charming 2 Bedroom Airbnb. The house provides present-day amenities while still honoring the original 1930s character. You’ll enjoy a new and sparkling clean kitchen, complete with all the appliances and utensils you need. The bathroom, laundry, dining room, reading nook and living room have all been beautifully updated as well, ensuring that you'll feel right at home from the moment you arrive.

The Little Brick House - Walkable to the Square

Welcome to this charming home near the downtown square of Winterset, Iowa. Known for The Bridges of Madison County, this town offers so much to do in a weekend. Our little town offers two wineries, two taprooms, a cidery, a brewery, a meadery and a Speakeasy. Many opportunities to enjoy the outdoors on the sweet little front porch of this home, shopping the square (just 4 blocks away), visiting bridges, hiking the Winterset City Park 2 mile loop or a picnic by the quiet Cedar Lake.

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.

Luxury 2 Bed/2 Bath Condo-1 Block to Downtown

Experience luxury in this 2-bedroom, 2-bath condo on Airbnb, designed for relaxation and comfortably sleeping four guests. Highlights include an elegant fireplace for cozy evenings and a fully equipped kitchen for gourmet meals. Nestled in a prime location, this condo promises both comfort and convenience, making it an ideal choice for travelers seeking a blend of luxury and practicality. Enjoy unwinding by the fire or exploring nearby attractions for an unforgettable stay.

Kim's Kottage on the RRVT, in Minburn, IA.

This home is perfect for the Cycling Enthusiast, a couple, family or small group of friends. This fully furnished cozy 2 bedroom home is sure to please. Located 1 block from the Raccoon River Valley Bike Trail (75 mile paved loop), 15 minutes from I-80 and 30/40 minutes from the State's Capital City of Des Moines, Minburn is the "Small Town with a Big Heart". There are two City Parks, an outdoor historical roller skating rink & 2 Rest/Bars.

Etta’s Place - private 1b/1b - MidCentury Modern

We love our neighborhood and are excited to share it with you! We have partnered with local restaurants, bars, coffee shops, boutiques, & tea shops to offer exclusive discounts to guests of “Etta’s Place.” It’s our hope that this Airbnb allows you to enjoy the wonderful Ingersoll District. Des Moines is a great place to visit, lots of outdoor activities, amazing food, and unique experiences around every corner!

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!