Vacation rentals in Madison County

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Top-rated vacation rentals in Madison County

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Guest favorite

The exterior of Rosehaven is showcased, featuring a charming red facade with white trim. A welcoming porch is adorned with greenery and flowers, framed by well-maintained shrubs and trees. A white picket fence outlines the property, emphasizing its inviting presence in the neighborhood.

Home in Winterset

4.98 out of 5 average rating, 106 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!

Top guest favorite

A spacious kitchen area is paired with a cozy living space. A tree and eagle relief art sculpture adorns the wall, while large windows provide natural light and views of the outdoors. Gray couches face a coffee table, and the kitchen features modern appliances and ample counter space.

Loft in Winterset

5 out of 5 average rating, 96 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.

Guest favorite

The inviting living area features a modern television mounted above a decorative fireplace. A comfortable brown sofa is paired with stylish accent chairs. A round black table sits at the center, surrounded by soft textures and greenery on the shelves, enhancing the cozy environment.

Apartment in Winterset

4.87 out of 5 average rating, 15 reviews

Luxury Private Space, close to West DM!

Step into our luxurious studio that seamlessly blends style and functionality. This elegant space greets you with the warm glow of a modern fireplace, perfect for cozy evenings after a day of exploration in the quaint town square located just a block away. The studio's clever design boasts a well-equipped workstation, the sleek and space-saving Murphy bed transforms the room from a productive workspace by day to a tranquil sleeping area by night. The promise of an exquisite stay awaits you.

Guest favorite

The historic stone house is illuminated by warm exterior lighting, showcasing its textured stone wall and charming architectural features. Surrounding lights provide a soft glow in the evening, while trees and foliage can be seen in the background, creating a serene outdoor atmosphere.

Home in Winterset

4.96 out of 5 average rating, 292 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.

Top guest favorite

A cozy living area features a rustic wooden bench beneath decorative wall art that reads 'Welcome home.' A dark patterned chair and a light grey couch are arranged to foster conversation, complemented by soft pillows and a coffee table displaying books.

Home in Winterset

5 out of 5 average rating, 45 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.

Top guest favorite

An inviting outdoor deck area features a wooden seating arrangement under a metal roof, adorned with string lights. A spacious couch offers comfort, while a long wooden table complements the rustic charm. Lush greenery and open space are visible in the background.

Cabin in Cumming

4.98 out of 5 average rating, 162 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.

The exterior of a cozy home is framed by a fenced yard, featuring flower beds with a variety of plants. A flag hangs from the porch, while decorative elements like a garden statue and a birdbath add character to the inviting outdoor space.

Apartment in Winterset

4.84 out of 5 average rating, 440 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.

Top guest favorite

The two-story farmhouse features a white exterior and a welcoming front porch, adorned with potted plants. A staircase leads to the entrance, flanked by a neat lawn. An American flag is displayed, adding to the home's charm and character.

Home in Earlham

4.96 out of 5 average rating, 114 reviews

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.

Top guest favorite

An open-plan living area is shown, featuring a comfortable gray sofa with orange pillows. A wooden dining table is accompanied by black chairs, while a ceiling fan adds to the airiness. Sliding barn doors lead to another room, and natural light enhances the inviting feel.

Home in Winterset

5 out of 5 average rating, 79 reviews

The Roost at Speckled Hen Farms.

Explore the Iowa countryside with this 70's ranch as your relaxing base camp. Situated on 5 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!

Top guest favorite

A charming cottage exterior is framed by lush green trees and manicured lawns. The inviting porch features white railings and steps leading to a front door, while large windows allow natural light to illuminate the interior.

Home in Winterset

5 out of 5 average rating, 38 reviews

Renovated Cottage: 3 blocks to shops on square

Our renovated 1910 "Cottage on Court" is more than just a place to stay; it’s a home where memories are made. This charming 2-bedroom, 1.5-bath cottage blends historic charm with modern amenities for a perfect stay. Nestled just 3 blocks from the downtown square, you’re close to shops, cafes, and attractions like the John Wayne Birthplace and Quilt Museum. Book your stay today and discover the allure of our charming cottage in the heart of historic Winterset, IA

Top guest favorite

A view of a charming farmhouse surrounded by vibrant pink flowers in full bloom. A white picket fence lines the flowerbed, while the house sits peacefully amidst a backdrop of lush greenery and clear blue skies.

Farm stay in Winterset

4.98 out of 5 average rating, 59 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.

Top guest favorite

A charming home exterior is illuminated at dusk, showcasing a stone and siding facade. A blue front door invites entry, flanked by two seating areas on the porch. A well-maintained lawn extends to the driveway, enhancing the welcoming appearance.

Home in Winterset

5 out of 5 average rating, 14 reviews

Covered Bridge Haven - 3BR House w/ Themed Rooms

Charming 3-bed, 3-bath home on Winterset's north side, just 1.2 miles from the town square and Madison County Courthouse. Only 2 miles from Cutler-Donahoe Covered Bridge and City Park. Enjoy a Madison County-themed master bedroom and an Iowa State Fair-themed bedroom. Perfect for families or groups seeking a cozy, themed retreat with easy access to Winterset’s historic charm and attractions. Relax in comfort and explore the heart of Iowa!