Winterset Vacations from $300

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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.
My Place Hotel - Ankeny/ Des Moines, IA

My Place Hotel - Ankeny/ Des Moines, IA

3 out of 5
Price was $378, price is now $300 per person
$300
per person
Oct 29 - Nov 3
found 17 hours ago
Roundtrip flight included
Phoenix (PHX) to Des Moines (DSM)
9/10 Wonderful! (726 reviews)
Very nice clean and safe - Great for an extended stay - kitchen in room and room was very spacious

Reviewed on Aug 6, 2025

Qube Hotel

Qube Hotel

2.5 out of 5
Price was $527, price is now $385 per person
$385
per person
Oct 29 - Nov 3
found 16 hours ago
Roundtrip flight included
Phoenix (PHX) to Des Moines (DSM)
8.4/10 Very Good! (698 reviews)
Bed was comfortable. Room lighting was poor, too dim in vanity/sink area. Towels were very thin, need to be discarded. Toilet was difficult to flush & was leaking. Breakfast items were ok, coffee wasn't that good. The overall experience was just ok, and we were glad to be leaving. The location was good & basic improvements could be made!

Reviewed on Aug 22, 2025

Des Moines Classy 2BD 2BA Downtown Apartment

Des Moines Classy 2BD 2BA Downtown Apartment

2 out of 5
Downtown Des Moines
Save 100% on your flight
Price was $987, price is now $796 per person
$796
per person
Oct 29 - Nov 3
found 17 hours ago
Roundtrip flight included
Phoenix (PHX) to Des Moines (DSM)
No reviews
Des Moines Alluring 2BD 2BA Downtown Apartment

Des Moines Alluring 2BD 2BA Downtown Apartment

2 out of 5
Downtown Des Moines
Save 100% on your flight
Price was $987, price is now $796 per person
$796
per person
Oct 29 - Nov 3
found 17 hours ago
Roundtrip flight included
Phoenix (PHX) to Des Moines (DSM)
No reviews
AmericInn by Wyndham Ankeny/Des Moines

AmericInn by Wyndham Ankeny/Des Moines

3 out of 5
Price was $465, price is now $376 per person
$376
per person
Oct 29 - Nov 3
found 16 hours ago
Roundtrip flight included
Phoenix (PHX) to Des Moines (DSM)
8/10 Very Good! (784 reviews)
Is a nice hotel with a decent size poll and a hut tub, grate for kids. However, there is no elevator and the pool area need some renovations.

Reviewed on Aug 18, 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

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

John Wayne Birthplace Museum

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
$140 nightly
The price is $157 total per night from Sep 1 to Sep 2
$157 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (668 reviews)
"Always great!"

Reviewed on Aug 16, 2025

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
$89 nightly
The price is $98 total per night from Aug 25 to Aug 26
$98 total
Aug 25 - Aug 26
Total with taxes and fees
9/10 Wonderful! (723 reviews)
"Only stayed one night . The beds were comfortable the room was clean and I would definitely stay there again."

Reviewed on Aug 17, 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 $156 total per night from Aug 31 to Sep 1
$156 total
Aug 31 - Sep 1
Total with taxes and fees
9.4/10 Exceptional! (1,023 reviews)
"Excellent"

Reviewed on Aug 21, 2025

Hotel Fort Des Moines, Curio Collection by Hilton
See all 529 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.

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Frequently asked questions

How much does a Winterset vacation package cost?
Offering great value package deals from $300 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.