Winterset Vacations
Book a Hotel + Flight or Car together to unlock savings
Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀
- Plan, book, travel with confidence
Better together
Save up to ₩234,741 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Find the Best Winterset Vacation Packages
Winterset Hotel Deals
Cobblestone Inn & Suites - Winterset, IA
1304 North 4th Avenue, Winterset, IA
Fully refundableReserve now, pay when you stay
The price is ₩139,526 per night from Sep 28 to Sep 29
₩139,526
₩156,260 total
Sep 28 - Sep 29
includes taxes & fees
9.2/10 Wonderful! (676 reviews)
"The bed was very comfortable. The staff was nice and helpful. Breakfast was good."
Reviewed on Sep 18, 2025
Covered Bridge Inn
1312 Cedar Bridge Rd., Winterset, IA
Fully refundableReserve now, pay when you stay
The price is ₩124,315 per night from Sep 23 to Sep 24
₩124,315
₩136,747 total
Sep 23 - Sep 24
includes taxes & fees
9/10 Wonderful! (734 reviews)
"Eggs were only the whites -- ick. Limited condiments for breakfast."
Reviewed on Sep 17, 2025
Hotel Fort Des Moines, Curio Collection by Hilton
1000 Walnut St, Des Moines, IA
Fully refundableReserve now, pay when you stay
The price is ₩200,650 per night from Sep 25 to Sep 26
₩200,650
₩224,728 total
Sep 25 - Sep 26
includes taxes & fees
9.4/10 Exceptional! (1,021 reviews)
"Really enjoyed our stay! We made reservations at the speak easy, cool private bar area but, the waitresses weren’t overly friendly. Enjoyed it was in walking distance of a lot of things we did. Loved the key card to access elevator for security purpose. The coffe shop in the hotel was good as well! ..."
Reviewed on Sep 13, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Other vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
