
Vacation rentals in Madison County
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Top-rated vacation rentals in Madison County
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Other great vacation rentals in Madison County
Top guest favorite

Cabin in Cumming
4.99 out of 5 average rating, 142 reviewsIconic 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

Apartment in Winterset
4.85 out of 5 average rating, 432 reviewsIowa 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 reviewsRenovated 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

Home in Winterset
5 out of 5 average rating, 34 reviewsThe 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

Home in Winterset
4.96 out of 5 average rating, 255 reviewsThe 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

Home in Winterset
4.96 out of 5 average rating, 27 reviewsModern 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

Farm stay in Winterset
4.98 out of 5 average rating, 44 reviewsEntire 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

Apartment in Winterset
5 out of 5 average rating, 9 reviewsLuxury 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.
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