Winterset Holiday Rentals

We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.

Destination
Dates
Guests
Search
  • Up-front pricing
  • No markup
  • Trusted partners

Compare Holiday Rentals, Villas & Resorts in Winterset

54 villas and rentals
Sort by
See More Properties

Luxury Holiday Rentals in Winterset

Over 45+ Luxury Holiday Rentals in or Near Winterset
See More Properties

Top-Rated Holiday Rentals with a Pool in Winterset

Over 5+ The Best Private Villas and Holiday Rentals in Winterset with a Pool
See More Properties

Pet-Friendly Holiday Rentals in Winterset

Over 4+ Pet-Friendly Holiday Rentals in or Near Winterset
See More Properties

Large Holiday Rentals and Private Villas in Winterset

Over 3+ Large Holiday Rentals and Private Villas in or Near Winterset
See More Properties

Winterset Private Villas and Holiday Homes Under $200

Over 19+ Winterset Private Villas and Holiday Homes Under $200
See More Properties

Instantly Bookable Holiday Homes in Winterset

Over 7+ Instantly Bookable Holiday Homes in or Near Winterset
See More Properties

Book a Last Minute Place to Stay in Winterset

About Casai's Private Villas and Holiday Rentals in Winterset

Discover more than 54 vacation rentals available in Winterset. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winterset.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winterset, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winterset. On average, places to stay near Winterset offer 630.52 ft², with nightly prices averaging R4,024.

With Casai, finding and comparing holiday rentals in Winterset is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Other Places to Stay in Winterset, IA


Madison County 91 Properties
Roseman Bridge 35 Properties
Patterson 35 Properties
Pammel Park 31 Properties
The Winterset Stage 26 Properties
Hogback Bridge 25 Properties
Cedar Bridge 25 Properties
Madison County Courthouse 24 Properties
John Wayne Birthplace Museum 24 Properties
Clark Tower 24 Properties
Holliwell Bridge 24 Properties

There are 54 Winterset, IA Holiday Rentals

Recently Booked Holiday Rentals in Winterset

Frequently Asked Questions About Winterset?

What are the top holiday rentals in Winterset?

With numerous options available in Winterset, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winterset:

How many Casai.co.za holiday rentals are available in Winterset?

As of 2026, Casai boasts over 54 properties listed in the Winterset area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winterset.