Vacation rentals in Madison County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Madison County

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

Guest favorite

Home in Winterset

5.0 out of 5 average rating, 44 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!

Aug 31 – Sep 7

G$29,789 GYD per night
Guest favorite

Cabin in Winterset

4.98 out of 5 average rating, 47 reviews

Cabin on 10 Wooded Acres to Relax, Unwind & Gather

This cozy cabin is the perfect place to relax & unwind in the woods. Fully furnished & equipped with everything you need for a comfortable stay, including a fully equipped kitchen, a washer & dryer, ping pong table, air hockey, board & yard games, outdoor fire pits, cable & WiFi. The cabin also has front & back decks with stunning views of the surrounding forest & creek. Just 5 minutes north of Winterset, the cabin is located in a private & quiet area, yet close to ammenities that you may need.

Jul 17 – 24

G$111,711 GYD per night
Guest favorite

Loft in Winterset

5.0 out of 5 average rating, 54 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.

Dec 25 – Jan 1

G$31,561 GYD per night

Popular amenities for Madison County vacation rentals

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