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.

Superhost

Apartment in Winterset

The Suite Iowa Life

Don’t spend your money on an impersonal hotel when you can stay at our “home away from home!” This Suite is located on the main level of our home where we live and work. It is a PRIVATE, FULLY EQUIPPED APARTMENT, UNSHARED SPACE. Separate entrance. Pets allowed. Access to yard and beautiful country views. * NEW MATTRESS * November 2023 BEST VALUE IN WINTERSET! Large backyard, grill, fire pit, close to town & centrally located amongst the six bridges. PLEASE READ FULL DESCRIPTION.

$84 per night

Superhost

Home in Afton

The Country Oasis

There's no better place to relax and unwind than at “The Country Oasis,” a charming 3-bedroom, 2-bathroom vacation rental perfect for your next getaway! Nestled in the rolling hills of southwest Iowa, this private home built in the early 1900s features all the updates and amenities you need for a relaxing stay! With a fireplace, hot tub, and several spaces to gather, both inside and out, this lovely home promises a memorable getaway with your friends and family!

$198 per night

Superhost

Apartment in Winterset

Winterset Wonderland

Located right off the main historic square in Winterset. The space is located in the old Madisonian building, built in 1906. This is a two bedroom, full kitchen apartment located above the Delirium Gallery. The space is also within a block away from the John Wayne Museum and the John Wayne Birth Place. It is also a prime location for the annual “Covered Bridge Festival” in the fall.

$186 per night