Holiday rentals 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.

This is the best Des Moines has to offer!

Welcome to a beautiful 3 story townhome in the heart of Des Moines. If an upscale modern home with an incredible view is your thing, you will be in heaven. Inside you’ll find a clean, bright and well decorated home with all the amenities you'll need to kick back, relax and enjoy your stay. Minutes from shopping, dining and nightlife. The bike trail is across the street where you can ride to Gray’s Lake or stroll to downtown DSM and enjoy the Farmer's Market, Civic Center and Principal Park.

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.

“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.

The Carol Anne-Charming 2bd/2ba Victorian near DT!

This Victorian-era duplex is the perfect mix of Victorian and modern for all the comforts of home. Perfect for quick or extended trips. Location can't be beat: Walking distance to Drake University. Minutes by car to downtown, hospitals, Ingersoll district and proximity to I-235 gets you anywhere in the city. Off street parking/electronic locks make check-in a easy. 2 large bedrooms w/queen beds, 2 bathrooms, kitchen, laundry, closets, and more making it ideal for multiple guests!

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.

Newly Remodeled Home with Walk-In Shower

My home is located in a safe and quiet neighborhood of Ankeny with a 16 min. drive to downtown Des Moines and Wells Fargo Arena. The high trestle trail is about 8 blocks away with a nice park 1 block away. The highlight of my home is the newly remodeled bedrooms and bathroom. There are queen beds in each of the bedrooms. The guest bed is brand new. The living room has a 55” LG OLED 4k TV with a PlayStation 5. I have high-speed cable internet with cable through slingTV.

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.

Luxury Hotel Condo in Downtown Des Moines

Relax in this 1920s historical Liberty Mutual building condo. Bask in the abundant light from the large windows atop this ninth floor condo in the Hyatt Place Hotel. View the sunset over the State Capital and the iconic Travelers sign. Pick out some vinyl to play on the stereo. Enjoy our collection of original artwork or read a book from our eclectic biography library. For a video walkthrough go to: YouTube: search 418 Liberty Luxury Hotel Condo

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!