Winterset Vacations

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Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀

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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$4,130 per night from Aug 24 to Aug 25
NT$4,130
NT$4,626 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (667 reviews)
"Always great!"

Reviewed on 2025/8/16

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$2,670 per night from Aug 18 to Aug 19
NT$2,670
NT$2,937 total
Aug 18 - Aug 19
includes taxes & fees
9/10 Wonderful! (719 reviews)
"The workers were so kind and helpful! We were there for a music festival so they were booked up, but when we called and requested an earlier checkin time they were flexible and made it happen for us! The staff are very accommodating and you can tell that they want their guests to be comfortable and ..."

Reviewed on 2025/8/4

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$4,181 per night from Aug 24 to Aug 25
NT$4,181
NT$4,683 total
Aug 24 - Aug 25
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Love the speakeasy and late night food options!"

Reviewed on 2025/8/15

Hotel Fort Des Moines, Curio Collection by Hilton
See all 532 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

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

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

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

Frequently asked questions

How much does a Winterset vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Winterset costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Winterset?
You're likely to find lower rates and greater availability in December, January and February. Explore our cheap Winterset vacation packages and you could land some great off-season discounts.
How many days is enough for Winterset?
The ideal length for your Winterset vacation depends on what you'd like to do and see. Usually, a few days to a week will give you time to visit all the main sights and discover some hidden spots along the way.
Is it worth booking a vacation package to Winterset?
Winterset is a good vacation destination with attractions like The Winterset Stage among the many things to keep you entertained. Whether you're traveling with the family or getting away with friends, a Winterset vacation promises a good time for everyone.
How to find the best Winterset package deals?
Use Expedia's filter tool to find some unbeatable Winterset package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Winterset package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Winterset vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays individually. Better still, you can tailor your Winterset trip to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Winterset?
If you're considering a spontaneous Winterset trip, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Winterset?

  1. Choose the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Winterset.
  2. Work out your budget: Ensure you have enough money to pay for everything from meals and transportation to activities and flights. Your accommodations will likely be the largest expense during your trip to Winterset.
  3. Decide how long to go away for: Now that you're more familiar with Winterset, you can work out the right length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Winterset vacation package that brings all your bookings together.

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