Winterset Vacations

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Find the Best Winterset Vacation Packages

Winterset Hotel Deals

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 SAR 334 per night from Apr 20 to Apr 21
SAR 334
SAR 367 total
includes taxes & fees
20 Apr - 21 Apr
9/10 Wonderful! (669 reviews)
Clean and affordable
"It was clean and affordable. Staff was nice. The only issue we had was someone had a dog that kept constantly barking for hours. We knew the hotel accepted pets so it’s not their fault. Just an FYI for anyone booking. It’s an older hotel as well, which is fine with us. We had a nice stay and would ..."

Reviewed on 14 April 2025

Covered Bridge Inn
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 SAR 371 per night from May 4 to May 5
SAR 371
SAR 416 total
includes taxes & fees
4 May - 5 May
9.2/10 Wonderful! (619 reviews)
"The property did not look like it did in the picture."

Reviewed on 13 April 2025

Cobblestone Inn & Suites - Winterset, IA
Stoney Creek Hotel Des Moines - Johnston
Stoney Creek Hotel Des Moines - Johnston
2.5 out of 5
5291 Stoney Creek Court, Johnston, IA
Fully refundableReserve now, pay when you stay
The price is SAR 407 per night from Apr 20 to Apr 21
SAR 407
SAR 456 total
includes taxes & fees
20 Apr - 21 Apr
8.8/10 Excellent! (1,657 reviews)
"The property is clean. I love the woodsy logged look. Smelled clean and the front desk staff was courteous. The room I had was spacious and even had a massage chair which believe me I took the liberty of using. It is very quiet. I didn't hear a peep. The main building has a pool and Sauna. You get ..."

Reviewed on 15 April 2025

Stoney Creek Hotel Des Moines - Johnston
See all 503 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.

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 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.

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

John Wayne Birthplace Museum

4.5/5(62 reviews)

You can spend an afternoon browsing the exhibits at John Wayne Birthplace Museum in Winterset. While you're in the area, wander around the natural setting.

John Wayne Birthplace Museum