Vacation rentals in Winterset

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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

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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

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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

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