Vacation rentals in Winterset

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Top-rated vacation rentals in Winterset

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Indianola

4.99 out of 5 average rating, 170 reviews

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 avialable 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.

Guest favorite

Cottage in Stuart

4.87 out of 5 average rating, 102 reviews

Huckleberry House: Saints Center, Lakes, Trails

Peaceful home in Stuart located just off I-80, only 25 minutes to West Des Moines! Stuart is a friendly small-town offering amenities including pubs, restaurants, ice cream shop, aquatic center/pool, movie theater, bowling alley, parks, Stuart Speedway, Wedding Venues, and more! Every year Stuart hosts many events including fun runs, tailgate parties, chili cook-offs & car shows. Nearby there are lakes and state parks with plenty of trails to explore. Relax and enjoy all the area has to offer!

Guest favorite

Home in Winterset

4.96 out of 5 average rating, 242 reviews

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.

Guest favorite

Cabin in Cumming

4.98 out of 5 average rating, 132 reviews

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.

Guest favorite

Rental unit in Winterset

4.85 out of 5 average rating, 425 reviews

Iowa Nice Winterset

You are renting a piece of “Iowa Nice”, please read my reviews, the entire Lower level but must pass through my area to go down stairs. I greet every guest so it is IMPORTANT to let me know your arrival time. IowaNice is a real thing not just a saying. I will be happy to cook Iowa home style meals for you, just let me know ahead of time. Also available for child care and dog sitting. Long term guest can have laundry done. I want you to know what small town Iowa is like.

Guest favorite

Cabin in Coon Rapids

4.98 out of 5 average rating, 283 reviews

The Rookery Cottage - Access scenic hiking trails

This rustic cottage is a quiet retreat in the heart of the Middle Raccoon River Valley. Situated on a private acreage within Whiterock Conservancy, guests can easily access 40mi+ of scenic hiking and mountain biking trails, float the nearby river, or enjoy dark sky viewing. A "rookery" is a nesting site for herons, a bird that prefers quiet, undisturbed habitat near water. And so the Rookery Cottage seeks to provide a natural escape from the daily grind.

Guest favorite

Home in Afton

4.99 out of 5 average rating, 128 reviews

The Country Oasis

The Country Oasis is an ideal destination for those seeking a serene retreat or a rejuvenating escape. This delightful vacation rental features 3 bedrooms and 2 bathrooms, making it perfect for your next getaway. With modern amenities and comforts such as a hot tub, fireplace, and various gathering spaces both indoors and out, The Country Oasis guarantees a memorable experience with friends and family. Come and enjoy the best of country living!

Guest favorite

Cottage in Minburn

4.96 out of 5 average rating, 290 reviews

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.

Guest favorite

Home in Dexter

4.91 out of 5 average rating, 117 reviews

The Victoria....

My place is located just off I-80 about 20 min from Jordan Creek town Center...the town of Dexter, Iowa has a park within walking distance, a public lake, The Rusty Duck Restaurant, Drew's Chocolates..You'll love my place because of staying in a roomy, unique Victorian home furnished with everything you’ll need! The backyard is now fully fenced providing privacy for your outdoor activities.

Guest favorite

Home in Dallas Center

4.95 out of 5 average rating, 286 reviews

Maple Street Hideaway

Lrg 2 bed, fenced backyard, and deck. Plenty of parking on property. Small town Iowa, easy access to WDSM/Waukee/Grimes/Johnston/Adel. Less than a 20 min. drive to an abundance of restaurants, shops, and attractions - not including the great places to eat/visit in town. Beautiful, quiet, tree lined street. Google Dallas Center to see all this Quietly Progressive town offers.

Guest favorite

Home in Winterset

4.98 out of 5 average rating, 236 reviews

Debbie’s Komfy Diggs Winterset

Whole home, two bedroom, full kitchen, pet friendly and close to beautiful downtown historic Winterset. Home of John Wayne and the Bridges of Madison County. My name is Debbie, I have lived in Winterset for over fifty years. Can keep you informed of coming events and maps of the area. Located 13 miles from Interstate 35 and Interstate 80.

Guest favorite

Tent in Perry

4.94 out of 5 average rating, 149 reviews

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.