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

The Hen House

The wonderfully remodeled home based on 55 acres overlooking mature trees and a large pond. The house has 3 bedrooms and 1 1/2 baths. Laundry is available to use as well. Kitchen is fully stocked for your cooking enjoyment and a gas grill is offered as well to use. This house is perfect for families, small groups, or business trips. Situated just 20 minutes from Des Moines airport, and 25 minutes from downtown Des Moines, you will be able to experience the quiet and beautiful scenery to enjoy.

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.

Taste of Iowa: NearDowntownDSM w/ Fun Reading Nook

Stay at The Taste of Iowa! A great location central to many DSM staples nestled off a quiet residential side street! The space has a queen bed in room 1, two Twin XL beds & a fun reading nook in room 2, & full bath. Easy remote check-in w/ both driveway parking & free street parking offered. A quick drive to: ☀ ~8 min to DSM Airport ☀ ~7 min to Wells Fargo Arena ☀ ~8 min to the Zoo ☀ ~7 min to the Grays Lake ☀ ~14 min to the Fairgrounds ☀ ~22 min to Jordan Creek ☀ ~20 min to Adventureland

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 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.

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.

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.

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.

Relaxing galaxy bell tent getaway

Come sleep under the stars in this cozy galaxy bell tent. You can enjoy a good nights sleep in the comfortable King bed and stay comfortable with an air conditioner and heater. There is also a fridge for keeping your food fresh. Soak up nature while you hike the trails around Oak Haven Acres, a 32 acre farm in rural Iowa. For your security we have a trail camera at the beginning of the driveway that won’t intrude on your privacy.

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!