Skip to content
Some info has been automatically translated. Show original language

Vacation rentals in Winterset

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winterset

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

Loft in Winterset
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.
$175 per night
Rental unit in Winterset
The Suite Iowa Life
This Suite is located on the main level of our home. It is a PRIVATE, FULLY EQUIPPED APARTMENT, UNSHARED SPACE. Separate entrance. Pets allowed. Access to yard and beautiful country views. Don’t spend your money on an impersonal hotel when you can stay at our “home away from home!” Conveniently located just minutes from quintessential downtown Winterset, the John Wayne Birthplace and Museum, and centrally located amongst the six famous bridges of Madison County. PLEASE READ FULL DESCRIPTION.
$83 per night
Cabin in Winterset
Whimsical cabin nestled in the woods
Iris Aisle is a whimsical, intimate venue + hemp farm located in Madison County Iowa. Our Victorian conservatory is used for many different events and classes and of course, plants. * please contact us first before booking. There can be events happening during your stay and/or there may be photographers on the property. We will make sure to let you know in advance if something is scheduled + during what times. This does not mean you have to leave the property.
$135 per night

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 vacation rentals in Winterset

Home in Winterset
$131 per night
Condo in Winterset
2 BR fully furnished private condo
$100 per night
Rental unit in Winterset
Iowa Nice Winterset
$69 per night
Home in Winterset
Hygge House in the ❤️ of historic Winterset
$180 per night
Rental unit in Winterset
Wonderland Winter Set
$179 per night
Home in Winterset
The Bungalow in Winterset
$204 per night
Home in Winterset
The Roost at Speckled Hen Farms.
$199 per night
Guest suite in Winterset
Entire Guest Home in Beautiful Madison County
$221 per night
Farm stay in Winterset
Historic Stone Farm House & Venue
$185 per night
Home in Dallas Center
Maggie's Place
$55 per night
Home in Cumming
Little Shouse On The Prairie
$120 per night
Rental unit in Indianola
Indianola 1 Bedroom Apartment Near Town Square
$41 per night
  1. Airbnb
  2. United States
  3. Iowa
  4. Madison County
  5. Winterset