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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.

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.
$83 per night
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
Home in Winterset
Hygge House in the ❤️ of historic Winterset
Hygge: a Norwegian word for a mood of coziness, and comfortable conviviality with feelings of wellness and contentment. Swing on the quaint side porch or congregate on the large back deck. Gather at the harvest table in the front room. Cook a meal in the kitchen. Walk the 3 blocks to the historic square and enjoy shops, restaurants, museums and parks or take a bike ride. Bring your girlfriends for a craft weekend or your family and enjoy all our wonderful town has to offer!
$180 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

Cabin in Winterset
Whimsical cabin nestled in the woods
$135 per night
Guesthouse in Winterset
Iowa Nice Winterset
$71 per night
Home in Winterset
The Bungalow in Winterset
$204 per night
Rental unit in Winterset
Wonderland Winter Set
$189 per night
Home in Winterset
$131 per night
Condo in Winterset
2 BR fully furnished private condo
$100 per night
Guest suite in Winterset
Entire Guest Home in Beautiful Madison County
$221 per night
Home in Winterset
The Roost at Speckled Hen Farms.
$199 per night
Guest suite in Des Moines
Cheerful & Cozy Studio - Fully Private Entrance
$38 per night
Cottage in Stuart
Huckleberry House: Saints Center, Lakes, Trails
$119 per night
Private room in Des Moines
Near airport, interstate, city
$30 per night
Rental unit in West Des Moines
✧Odyssey at Keystone | Elegant 1BD Apartment✧
$69 per night
  1. Airbnb
  2. United States
  3. Iowa
  4. Madison County
  5. Winterset