Winterset Vacations from $693

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Your Winterset Vacation

Book a Winterset vacation package and get set for an awesome adventure. Famous for its rich history and friendly locals, there's loads to like about this fascinating city. Every trip to Winterset needs a well-planned itinerary. Fill yours with leading attractions like John Wayne Birthplace Museum, The Winterset Stage and Clark Tower. Stop dreaming and start traveling. Check out the wide range of options on Expedia today and finally put your Winterset vacation plans into motion!

The Latest Winterset vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place West Des Moines Jordan Creek

Hyatt Place West Des Moines Jordan Creek

3 out of 5
Price was $779, price is now $693 per person
$693
per person
Apr 6 - Apr 10
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Des Moines (DSM)
9.2/10 Wonderful! (1,004 reviews)
Clean room, staff helpful and friendly. A smile goes a long ways! Thanks!

Reviewed on Jan 12, 2026

Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA

2.5 out of 5
Price was $893, price is now $776 per person
$776
per person
Mar 1 - Mar 8
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Des Moines (DSM)
9.2/10 Wonderful! (708 reviews)
The entire hotel is spotless and nice. Customer service was over the top! I might come here to just get away for a night. The beds were comfortable too!

Reviewed on Jan 1, 2026

Wildwood Lodge

Wildwood Lodge

3 out of 5
Price was $817, price is now $719 per person
$719
per person
Apr 6 - Apr 10
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Des Moines (DSM)
9.6/10 Exceptional! (1,194 reviews)
Staff was courteous

Reviewed on Jan 10, 2026

Hilton Des Moines Downtown

Hilton Des Moines Downtown

3.5 out of 5
Downtown Des Moines
Price was $812, price is now $722 per person
$722
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Des Moines (DSM)
9/10 Wonderful! (1,000 reviews)
Sink in bathroom would not drain

Reviewed on Jan 4, 2026

Fairfield Inn & Suites by Marriott Des Moines Downtown

Fairfield Inn & Suites by Marriott Des Moines Downtown

4 out of 5
Downtown Des Moines
Price was $1,207, price is now $1,087 per person
$1,087
per person
Mar 1 - Mar 8
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Des Moines (DSM)
9/10 Wonderful! (391 reviews)
Nice hotel with a nice lounge. Quiet, convenient, nice beds.

Reviewed on Dec 30, 2025

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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

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
$103 nightly
The price is $116 total per night from Feb 13 to Feb 14
$116 total
Feb 13 - Feb 14
Total with taxes and fees
9.2/10 Wonderful! (713 reviews)
The entire hotel is spotless and nice. Customer service was over the top! I might come here to just get away for a night. The beds were comfortable too!

Reviewed on Jan 1, 2026

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
$79 nightly
The price is $88 total per night from Jan 14 to Jan 15
$88 total
Jan 14 - Jan 15
Total with taxes and fees
8.8/10 Excellent! (769 reviews)
Was in town for a week for work. Great Lil Hotel well worth the Money. Staff were very Friendly.

Reviewed on Dec 22, 2025

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
$139 nightly
The price is $155 total per night from Jan 17 to Jan 18
$155 total
Jan 17 - Jan 18
Total with taxes and fees
9.4/10 Exceptional! (1,076 reviews)
Very nice hotel.

Reviewed on Jan 12, 2026

Hotel Fort Des Moines, Curio Collection by Hilton
See all 553 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.

Find the Best Winterset Vacation Packages

Winterset Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Des Moines Intl. Airport (DSM)
Population
5,200
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Pammel State Park, The Winterset Stage and Roseman Bridge

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Frequently asked questions

How much does a Winterset vacation package cost?
Offering great value package deals from $693 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?
If you're looking to score a cheap Winterset vacation package, consider planning a trip in November, December and January. You're likely to find lower prices on flights and accommodations during these quieter months — perfect for a budget-friendly break.
How many days is enough for Winterset?
With a well-organized travel plan, you can easily hit the top Winterset attractions in a handful of days. But if you want to discover hidden gems or go on day trips, consider booking your Winterset vacation for longer.
Is it worth booking a vacation package to Winterset?
Winterset has everything you need for a wonderful getaway. Begin your Winterset vacation on a high note by checking out popular attractions like The Winterset Stage.
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.
Does Expedia offer Book Now, Pay Later Winterset vacation packages?
Your Winterset trip should be an escape from your daily routine, not a reason for money-related stress. So to allow you extra flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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