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Vacation rentals in Madison County

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Top-rated vacation rentals in Madison County

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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, 101 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, 92 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.

Top 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, 285 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, 43 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, 160 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.

Top guest favorite

The exterior of the home features a welcoming porch with a sitting area, flanked by decorative columns. A vibrant American flag is displayed, while lush greenery and colorful flowers enhance the yard's appeal. Large windows invite natural light into the entrance.

Home in Winterset

4.98 out of 5 average rating, 62 reviews

Hygge House in the ❤️ of historic Winterset

Hygge: a Norwegian word for a mood of coziness, and comfortable conviviality with feelings of wellness and contentment. Swing on the quaint side porch or congregate on the large back deck. Gather at the harvest table in the front room. Cook a meal in the kitchen. Walk the 3 blocks to the historic square and enjoy shops, restaurants, museums and parks or take a bike ride. Bring your girlfriends for a craft weekend or your family and enjoy all our wonderful town has to offer!

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

A cozy glamping tent is elevated on a wooden deck surrounded by lush greenery. The front features a large opening that provides views of the interior. Stairs lead down to the grass, inviting further exploration of the flower farm.

Tent in Winterset

5 out of 5 average rating, 39 reviews

Glamping Flower Farm Stay- PepperHarrow

Escape to the beauty and tranquility of PepperHarrow, a 20 acre flower farm in Madison County. Our glamping tent offers a unique and peaceful getaway, surrounded by 8.5 acres of stunning flowers. Relax and unwind amongst 2.5 acres of lavender, 1.5 acres of annuals, 1 acre of perennials, and wildflower areas supporting local pollinators. Experience the magic of nature from the comfort of our cozy glamping tent, perched atop the bluffs overlooking the Middle River Valley.

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, 112 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, 77 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, 36 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

A welcoming cabin is nestled among trees, featuring a porch with a couple of chairs. A gravel path leads towards the entrance, surrounded by greenery and sunlit foliage. The cabin’s exterior is painted in a soothing green tone, harmonizing with the natural surroundings.

Place to stay in Winterset

4.89 out of 5 average rating, 74 reviews

Whimsical cabin nestled in the woods

Iris Aisle is a whimsical, intimate venue + hemp farm in Madison County, Iowa. Our Victorian conservatory hosts events, classes, and of course—plants. ✨ Now offering elopement add-ons for couples seeking a dreamy, intimate setting. Please contact us before booking—events or photographers may be onsite. We’ll notify you of any scheduled activity + times, but you are always welcome to enjoy the space. For non-Airbnb stays, visit our website.

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Popular amenities for Madison County vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Madison County

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, 160 reviews

Iconic Iowa - A 1920 Built Country Cabin

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

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, 36 reviews

Renovated Cottage: 3 blocks to shops on square

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, 112 reviews

Friendly Quarters

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, 43 reviews

The Home Place

Top 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, 285 reviews

The Legacy Stone House

Top guest favorite

A cozy glamping tent is elevated on a wooden deck surrounded by lush greenery. The front features a large opening that provides views of the interior. Stairs lead down to the grass, inviting further exploration of the flower farm.

Tent in Winterset

5 out of 5 average rating, 39 reviews

Glamping Flower Farm Stay- PepperHarrow

Top guest favorite

The exterior of the home is shown, featuring a light green siding and a well-kept yard. Two white chairs with red cushions provide seating near the entrance. A concrete pathway leads to the front door, which is framed by a small overhang.

Home in Winterset

4.98 out of 5 average rating, 283 reviews

Debbie’s Komfy Diggs Winterset

Destinations to explore