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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.

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
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
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

Stay near Winterset's top sights

John Wayne Birthplace & Museum14 locals recommend
Winterset City Park4 locals recommend
Northside Cafe5 locals recommend
Hy-Vee5 locals recommend
Sports Page4 locals recommend
Mi Pueblito5 locals recommend

Other great vacation rentals in Winterset

Cottage in Minburn
Kim's Kottage on the RRVT, in Minburn, IA.
$60 per night
Townhouse in Ames
Downtown & Campus★Wifi★W/D★Netflix★2Br/1Ba★
$70 per night
Guest suite in Waukee
Waukee 2 Bedroom Private Sweet Suite.
$98 per night
Guest suite in Des Moines
Executive Guest Suite w/ Laundry
$95 per night
Home in Dallas Center
Maple Street Hideaway
$60 per night
Home in Winterset
$119 per night
Guest suite in Winterset
2 BR fully furnished private condo
$90 per night
Loft in Winterset
Aerie Loft Apartment with view that sleeps 7
$175 per night
Home in Winterset
The Little Red House
$130 per night
Cabin in Winterset
Whimsical cabin nestled in the woods
$135 per night
Home in Winterset
Hygge House in the ❤️ of historic Winterset
$180 per night
Home in Winterset
The Roost at Speckled Hen Farms.
$199 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Iowa
  4. Madison County
  5. Winterset