Winterset Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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!
Top Winterset Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Downtown - Mercy Area by IHG
Downtown Des Moines
Price was CA $1,442, price is now CA $1,196 per person
CA $1,196
per person
Jul 28 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Des Moines (DSM)
7.8/10 Good! (1,015 reviews)
They didn’t have an airport shuttle even though they stated they did.
Reviewed on May 17, 2026
Hotel Fort Des Moines, Curio Collection by Hilton
Downtown Des Moines
Price was CA $2,583, price is now CA $1,913 per person
CA $1,913
per person
Jul 28 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Des Moines (DSM)
9.6/10 Exceptional! (1,144 reviews)
Very clean, friendly staff and AMAZING lattes!
Reviewed on May 18, 2026
Hampton Inn West Des Moines Lake Drive
Price was CA $2,029, price is now CA $1,600 per person
CA $1,600
per person
Jul 28 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Des Moines (DSM)
8.8/10 Excellent! (1,003 reviews)
Clean rooms but smaller than what I'm used to for a hampton. The staff could be more welcoming but then again I didn't have much interaction with them. The pool had no towels and the basket that had the dirty towels were overflowing. Would've been nice to have towels stocked for a weekend.
Reviewed on May 12, 2026
Homewood Suites By Hilton Urbandale Des Moines
Price was CA $1,643, price is now CA $1,390 per person
CA $1,390
per person
Jul 28 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Des Moines (DSM)
10/10 Exceptional! (7 reviews)
The cleanest motel room i have ever been in and the breakfast was one of the best also. The staff were very friendly and i love the check in on you text received not too long after we were up in our room.
Reviewed on Apr 5, 2026
Baymont by Wyndham Des Moines Airport
Southwestern Hills
Price was CA $1,679, price is now CA $1,426 per person
CA $1,426
per person
Jul 28 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Des Moines (DSM)
9.4/10 Exceptional! (1,166 reviews)
Staff was friendly and helpful. We were able to check in early. Room was clean.
Reviewed on May 17, 2026
Winterset Hotel Deals
Cobblestone Inn & Suites - Winterset, IA
1304 North 4th Avenue Winterset IA
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Jun 8 to Jun 9
CA $154
CA $173 total
Jun 8 - Jun 9
includes taxes & fees
9.2/10 Wonderful! (742 reviews)
Breakfast was good, staff excellent, room very nice.
Reviewed on May 16, 2026
Covered Bridge Inn
1312 Cedar Bridge Rd. Winterset IA
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from May 19 to May 20
CA $140
CA $156 total
May 19 - May 20
includes taxes & fees
9/10 Wonderful! (789 reviews)
It was a very quiet room,with awesome people in staff
Reviewed on May 12, 2026
Hotel Fort Des Moines, Curio Collection by Hilton
1000 Walnut St Des Moines IA
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from May 24 to May 25
CA $201
CA $225 total
May 24 - May 25
includes taxes & fees
9.6/10 Exceptional! (1,161 reviews)
Very clean, friendly staff and AMAZING lattes!
Reviewed on May 18, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
