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$3,653 per night from Dec 1 to Dec 2
NT$3,653
NT$4,092 total
Dec 1 - Dec 2
includes taxes & fees
9.2/10 Wonderful! (708 reviews)
only thing we disliked was the staff started putting away breakfast 15 minutes early and continued while we were eating, then getting the "stink eye" while eating from the staff.

Reviewed on 2025/10/31

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$3,002 per night from Dec 1 to Dec 2
NT$3,002
NT$3,302 total
Dec 1 - Dec 2
includes taxes & fees
9/10 Wonderful! (762 reviews)
The staff was helpful and kind, even asking if we needed help with our luggage. The room was very clean and spacious. We were very comfortable. Breakfast was a lot of variety, and tasted good. We found out you are a pet friendly motel, so on our next trip, we can bring our dog! A big plus!!!

Reviewed on 2025/11/16

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$4,328 per night from Nov 25 to Nov 26
NT$4,328
NT$4,847 total
Nov 25 - Nov 26
includes taxes & fees
9.4/10 Exceptional! (1,041 reviews)
Room was clean and comfortable! We also enjoyed the unique atmosphere and decor!

Reviewed on 2025/11/17

Hotel Fort Des Moines, Curio Collection by Hilton
See all 533 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

Cedar Bridge

4.5/5(5 reviews)

You can learn about the history of Winterset when you stop by Cedar Bridge. Make some time to visit the monuments while you're in the area.

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