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Holiday rentals in Winterset

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Top-rated holiday rentals in Winterset

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

Guest house in Winterset
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. IowaNice is a real thing not just a saying and we will prove it to you when you come to visit Winterset. What you will love is the friendliness of every person you meet in Madison County. It is a short walk to the Square with our Qwaint little shops and our historic courthouse. The beautiful city Park has one of our iconic covered bridges seven blocks from here.
₹5,880 per night
SUPERHOST
Home in Winterset
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!
₹10,783 per night
Rental unit in Winterset
The Suite Iowa Life
Our acreage did not suffer any damage from the large Winterset Tornado on March 5, 2022. Praise God! This Suite is located on the main level of our home. It is not the entire house and does not include the upstairs space located above. There are no shared spaces and you will have your privacy. We are located just one mile outside of Winterset and 25 minutes from West Des Moines. We also run a small auto body and restoration business on the property but it should not interfere with your stay.
₹7,232 per night
SUPERHOST

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Stay near Winterset's top sights

Photo of John Wayne Birthplace & Museum
John Wayne Birthplace & Museum14 locals recommend
Photo of Winterset City Park
Winterset City Park4 locals recommend
Photo of Hy-Vee
Hy-Vee5 locals recommend
Photo of Sports Page
Sports Page4 locals recommend
Photo of Northside Cafe
Northside Cafe5 locals recommend
Photo of Mi Pueblito
Mi Pueblito5 locals recommend

Other great holiday rentals in Winterset

Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
₹14,405 per night
SUPERHOST
Apartment in Winterset
2 BR fully furnished private condo
₹8,232 per night
SUPERHOST
Home in Winterset
Hygge House in the ❤️ of historic Winterset
₹14,817 per night
SUPERHOST
Rental unit in Winterset
Winter Wonderland Set
₹15,582 per night
Home in Winterset
The Roost at Speckled Hen Farms.
₹10,560 per night
Home in Winterset
The Bungalow in Winterset
₹16,757 per night
SUPERHOST
Cabin in Winterset
Wooded Cabin on 10 Acres to Explore and Entertain
₹31,456 per night
SUPERHOST
Farm stay in Winterset
Entire farmhouse in the country
₹17,728 per night
Cottage in Stuart
Huckleberry House: Saints Center, Lakes, Trails
₹5,115 per night
Guest suite in Winterset
Entire Guest Home in Beautiful Madison County
₹16,463 per night
Cabin in Cumming
Iconic Iowa - A 1920 Built Country Cabin
₹10,325 per night
SUPERHOST
Private room in Waukee
A private room and bathroom in a shared 2 bedroom.
₹2,552 per night
  1. Airbnb
  2. United States
  3. Iowa
  4. Madison County
  5. Winterset