Winterset Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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.
Hotel Fort Des Moines, Curio Collection by Hilton
Downtown Des Moines
Price was CA $2,057, price is now CA $1,575 per person
CA $1,575
per person
Jun 19 - Jun 26
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Des Moines (DSM)
9.6/10 Exceptional! (1,094 reviews)
Staff was very friendly and hotel was beautiful!
Reviewed on Mar 31, 2026
Hilton Des Moines Downtown
Downtown Des Moines
Price was CA $2,644, price is now CA $2,102 per person
CA $2,102
per person
Jun 19 - Jun 26
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Des Moines (DSM)
9/10 Wonderful! (999 reviews)
A front receptionist was repeatedly rude to the customers she managed over the phone. She was argumentative and denigrated her customers on the phone….including me. She argued with how I made my reservation - a phone call to Hilton reservations- she stated was made through a third party. That sort of rudeness required a re-think of her people-facing role. She became frustrated, her voices was raised, argumentative and simply rude. Never should she have access to customers.
Reviewed on Mar 26, 2026
Home2 Suites by Hilton Des Moines at Drake University
Drake
Price was CA $1,603, price is now CA $1,345 per person
CA $1,345
per person
Jun 19 - Jun 26
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Des Moines (DSM)
9.4/10 Exceptional! (1,011 reviews)
The breakfast menu was awesome! Waffles, fresh fruit, eggs-small scrambled and hard boiled, bacon, toast, juices, coffee and more! Best continental I’ve seen in awhile! The hotel was spotless, as was our room! Excellent and all staff was very cheerful and helpful!! Our dog loved it there too!!
Reviewed on Mar 30, 2026
Hampton Inn Des Moines-Airport
Greater South Side
Price was CA $1,699, price is now CA $1,469 per person
CA $1,469
per person
Jun 19 - Jun 26
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Des Moines (DSM)
8.8/10 Excellent! (1,007 reviews)
Shuttle at front door.
Reviewed on Mar 23, 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 $160 per night from Apr 7 to Apr 8
CA $160
CA $179 total
Apr 7 - Apr 8
includes taxes & fees
9.2/10 Wonderful! (724 reviews)
The breakfast would have been good had it not been for the awful eggs. They were dry and inedible. Otherwise, the hotel was clean and efficient for a one night stay.
Reviewed on Mar 29, 2026
Covered Bridge Inn
1312 Cedar Bridge Rd. Winterset IA
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Apr 7 to Apr 8
CA $98
CA $110 total
Apr 7 - Apr 8
includes taxes & fees
9/10 Wonderful! (784 reviews)
Our stay was very pleasant. The variety of choices at breakfast was actually quite a surprise! Great job!
Reviewed on Mar 30, 2026
Modern home on acreage with pond, trails, rolling hills, and sunset views
Winterset IA
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.
