Vacation rentals in Madison County

Find and book unique accommodations on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Madison County vacation rentals

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
4.99 out of 5 average rating, 142 reviews

Iconic Iowa - A 1920 Built Country Cabin

AaronRating, 5 stars1 month ago
Andrew's place is a hidden gem. The house is extremely cozy, warm, rustic, romantic, easy going, upscale and fun. It's location and exterior feel "country" and free but it's the decor and coziness of the interior that really set the place apart as one of the best AirBnBs I've ever stayed at. If you want to stay in St. Louis, Andrew's place is a great getaway minutes from town and all things nearby. If you live in St. Louis area, Andrew's place is perfect for a rendevous, for a meditative solo juant or a couple of buddies who want to laugh and shout around a bonfire. You won't be disappointed. As a very, very small drawback, the water pressure is on the low side. Andrew's attention to detail is obvious and I'm sure his continued upgrades will inprove this. We visited the area for my kid's wrestling tournament. We were very comfortable, everyone had their own bed for 2 adults and 3 teenagers. The place was perfect!
Guest favorite
A spacious walk-in shower is featured, equipped with a rain showerhead providing a cascading water effect. A hand-held shower attachment is also available. The walls are lined with textured tiles, and a decorative tile border adds visual interest.
Apartment in Winterset
4.85 out of 5 average rating, 432 reviews

Iowa Nice Winterset

EricaRating, 5 stars6 days ago
Three rooms- no door to separate basement space from upstairs but me and my kitties stayed in one room. Suzy was very nice and welcoming. Very much appreciated the stay.
Top guest favorite
Home in Winterset
5 out of 5 average rating, 27 reviews

Renovated Cottage: 3 blocks to Winterset square

CarmenRating, 5 stars1 month ago
We enjoyed Jane’s house so much!! She had local art and books on local history and locations!! Everything we needed!! Jane also sent a list of things to do and local restaurants!! We hope to go back to her house to kayak!!
Top guest favorite
The bathroom area features a rustic wooden cabinet displaying information about local attractions. Above the cabinet, a small shelf holds decor items, including a mirror and a plant. Soft lighting illuminates the space, enhancing the neutral color palette of the walls and fixtures.
Home in Winterset
5 out of 5 average rating, 34 reviews

The Home Place

SatomiRating, 5 stars1 month ago
This is the second time I’ve booked The Home Place. It is the perfect home away from home while staying in beautiful Winterset!
Top guest favorite
The historic stone house is surrounded by lush green grass and mature trees, providing a serene outdoor setting. A gravel path leads to the house, featuring large windows with wooden trim and a simple front door. Decorative items, like vintage wheels, can be seen near the entrance.
Home in Winterset
4.96 out of 5 average rating, 255 reviews

The Legacy Stone House

HollyRating, 5 stars4 weeks ago
This was a stop on our way west from Michigan. It could not have been more perfect. If you have a chance to stay here, DO IT. Every detail was tended to with love and affection. We enjoyed the privacy, the spacious rooms, cleanliness, comfortable bed, delicious coffee, internet, FANTASTIC location and plenty of room for us to start gaze on the clear night⭐️⭐️ I can't say enough about our stay. Angels and Rick were the perfect hosts. We are so greatful
Top guest favorite
A spacious deck is presented with outdoor seating arrangements, featuring two woven chairs and a small table. A propane grill is positioned nearby. A scenic view of a green field and trees extends beyond the deck, enhancing the connection to nature.
Home in Winterset
4.96 out of 5 average rating, 27 reviews

Modern Farmhouse Retreat-Private & Cozy-Sleeps 12!

MarlaRating, 5 stars1 month ago
This was a great place for our long weekend getaway. It was close to the Covered Bridges and a few other things we were interested in doing. The house was very clean and bright and had everything we needed. We contacted Lindsy for one minor item and she responded quickly and took care of it immediately.
Top guest favorite
A stone patio features six red Adirondack chairs arranged around a central fire pit. In the background, a red barn stands against a picturesque landscape of rolling hills and a fenced yard. A windmill is also visible in the distance under a partly cloudy sky.
Farm stay in Winterset
4.98 out of 5 average rating, 44 reviews

Entire farmhouse in the country

JenniferRating, 5 stars1 week ago
We had a wonderful time and enjoyed the beautiful farm house, the porch and the setting. We would love to come visit again.
Guest favorite
A modern kitchen island is showcased with a sleek countertop. A small succulent and a vase with greenery sit on the surface, accompanied by two white plates and bowls. Natural light filters through large windows, creating a bright and airy ambiance.
Apartment in Winterset
5 out of 5 average rating, 9 reviews

Luxury 2 Bed/2 Bath Condo

ScottRating, 5 stars3 weeks ago
It was everything that I could have asked for. The town is great and everything is walkable. Everyone that I met was amazingly friendly. The apartment was very clean and new. The closets were huge. The only downside that I ran into is lack of a dresser. There is a space for that type of clothing, but it is limited. The view is one of a kind and I can't think of anything that they didn't think of from coffee, to filters and all kitchen amenities that you could ever ask for.

Destinations to explore

  1. Airbnb
  2. United States
  3. Iowa
  4. Madison County