Winterset Vacations

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Find the Best Winterset Vacation Packages

Winterset Hotel Deals

Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA

2.5 out of 5
1304 North 4th Avenue, Winterset, IA
Fully refundableReserve now, pay when you stay
The price is NT$3,034 per night from Oct 19 to Oct 20
NT$3,034
NT$3,398 total
Oct 19 - Oct 20
includes taxes & fees
9.2/10 Wonderful! (683 reviews)
"Clean room great staff"

Reviewed on 2025/10/1

Cobblestone Inn & Suites - Winterset, IA
Covered Bridge Inn

Covered Bridge Inn

2.5 out of 5
1312 Cedar Bridge Rd., Winterset, IA
Fully refundableReserve now, pay when you stay
The price is NT$1,792 per night from Nov 1 to Nov 2
NT$1,792
NT$1,971 total
Nov 1 - Nov 2
includes taxes & fees
9/10 Wonderful! (742 reviews)
"Breakfast was top notch for the price."

Reviewed on 2025/9/29

Covered Bridge Inn
Hotel Fort Des Moines, Curio Collection by Hilton

Hotel Fort Des Moines, Curio Collection by Hilton

4.5 out of 5
1000 Walnut St, Des Moines, IA
Fully refundableReserve now, pay when you stay
The price is NT$4,363 per night from Oct 13 to Oct 14
NT$4,363
NT$4,887 total
Oct 13 - Oct 14
includes taxes & fees
9.4/10 Exceptional! (1,039 reviews)
"Ccccccc"

Reviewed on 2025/9/28

Hotel Fort Des Moines, Curio Collection by Hilton
See all 527 properties in Winterset
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.

Discover the most popular places to visit in Winterset

#adventure Built in 1883 by Harvey P. Jones and George K. Foster, Roseman is 107 feet in length and sits in its original location. It was renovated in 1992 at a cost of $152,515. In Robert James Waller’s novel, The Bridges of Madison County, and the movie of the same name, Roseman is the bridge Robert Kincaid seeks when he stops at Francesca Johnson’s home for directions. It is also where Francesca leaves her note inviting him to dinner. Also known as the “haunted” bridge, Roseman is where two sheriff’s posses trapped a county jail escapee in 1892. It is said the man rose up straight through the roof of the bridge, uttering a wild cry, and disappeared. He was never found, and it was decided that anyone capable of such a feat must be innocent.

Roseman Bridge

4/5(5 reviews)

You can learn about the history of Winterset with a stop at Roseman Bridge. Make some time to visit the monuments while you're in the area.

Roseman Bridge
On a stop over going to Whistler Mountain #blue #wanderwoman #Canada #takemeback

Clark Tower

4/5(4 reviews)

You can find out about the history of Winterset with a stop at Clark Tower. Make some time to visit the shops while you're in the area.

Clark Tower

The Winterset Stage

4.5/5(8 reviews)

You can enjoy a show at The Winterset Stage during your stay in Winterset. Make some time to visit the shops while you're in the area.

The Winterset Stage
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.