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 favourite

Home in Winterset

5.0 out of 5 average rating, 45 reviews

Rosehaven

Enjoy the nostalgic small town charm of Winterset, Iowa while staying at Rosehaven, within walking distance to the town square. Between the historic Madison County covered bridges in the area, the John Wayne museum and his preserved birthplace, as well as the numerous wineries and local events - Winterset is full of reasons to visit and stay at Rosehaven - a short 30 min. drive to Des Moines. Rosehaven is easy to find, with plenty of room for up to 5 or 6 guests. We look forward to having you!

Sep. 22 – 29

$226 CAD per night

Guest favourite

Loft in Winterset

5.0 out of 5 average rating, 57 reviews

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.

May 9 – 16

$242 CAD per night

Guest favourite

Home in Coon Rapids

4.97 out of 5 average rating, 132 reviews

1875 House, 316 Sumpter Ave, Coon Rapids IA

Home built in 1875. Cozy home, close to Middle Raccoon River. Walking and biking trail and river access in the park for canoes or kayaks within 300 yards from front door. Access to White Rock Conservancy trails. Six blocks from downtown shops with grocery and dining available. Beautiful nine hole golf course. We offer off street parking. Garage available for bicycles. Contact host. Large shaded back yard with small deck area and charcoal grill. There is a fire pit in the back yard.

Sep. 28 – Oct. 5

$104 CAD per night

Guest favourite

Home in Winterset

5.0 out of 5 average rating, 17 reviews

The Home Place

The Home Place, built in 1895, sits three blocks from the Winterset square. It showcases local businesses and Winterset history while offering modern amenities and the comforts of home. Soaps and cleaning supplies are as fragrant free as possible, allowing for a near hypoallergenic haven. No pets for this reason. We offer a king bed, a queen bed, a dedicated office, and a handicapped entrance ramp. Cots, Pack-N-Play, and baby gates are available upon request. Welcome to The Home Place.

Jul. 2 – 9

$209 CAD per night

Guest favourite

Home in Winterset

5.0 out of 5 average rating, 42 reviews

The Roost at Speckled Hen Farms.

Explore the Iowa countryside with this 70's ranch as your relaxing base camp. Situated on 10 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!

Jan. 12 – 19

$298 CAD per night

Guest favourite

Place to stay in Winterset

4.9 out of 5 average rating, 62 reviews

Whimsical cabin nestled in the woods

Iris Aisle is a whimsical, intimate venue + hemp farm located in Madison County Iowa. Our Victorian conservatory is used for many different events and classes and of course, plants. * please contact us first before booking. There can be events happening during your stay and/or there may be photographers on the property. We will make sure to let you know in advance if something is scheduled + during what times. This does not mean you have to leave the property.

Jul. 9 – 14

$241 CAD per night

Guest favourite

Home in Winterset

4.97 out of 5 average rating, 193 reviews

The Legacy Stone House

The 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.

Dec. 27 – Jan. 1

$255 CAD per night

Guest favourite

Farm stay in Winterset

4.95 out of 5 average rating, 21 reviews

Entire farmhouse in the country

Just 10 minutes north of Winterset, stay in a Covered Bridge House. You’ll love visiting the historic bridges & John Wayne Birthplace Museum. Perfect for families and groups, enjoy relaxing at our newly renovated “modern farmhouse style” home. A quiet retreat, nestled in beautiful rolling hills. Built by Eli Cox family, renowned covered bridge builders. It’s a short 5 minute drive to local attractions: Winterset Cidery, Covered Bridges Winery & Guye Woods.

May 28 – Jun. 4

$369 CAD per night

Guest favourite

Home in Indianola

4.99 out of 5 average rating, 142 reviews

The Hen House

The wonderfully remodeled home based on 55 acres overlooking mature trees and a large pond. Just a three minute drive to Lake Ahquabi that offers many family fun outdoor activities, hiking and biking trails. 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 that rural Iowa has to offer.

Oct. 11 – 18

$206 CAD per night

Guest favourite

Cabin in Coon Rapids

4.98 out of 5 average rating, 256 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.

Sep. 18 – 25

$157 CAD per night

Guest favourite

Cottage in Minburn

4.96 out of 5 average rating, 271 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.

Dec. 19 – 26

$113 CAD per night

Guest favourite

Farm stay in Dallas Center

4.9 out of 5 average rating, 144 reviews

Cozy Farmhouse Apartment near Des Moines

Cozy Farmhouse Apartment perfectly located for easy access to W. Des Moines/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. This spacious 1 bedroom apartment is located on an acerage between Dallas Center and Minburn. Located within 2 miles of Three Sisters Barn, 6 miles of Keller Brick Barn and Raccoon River Trail.

Jul. 3 – 10

$102 CAD per night