Winterset Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Winterset Holiday

Our pick of the best 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 NZ$163 per night from 14 July to 15 July
NZ$163
14 July - 15 July
includes taxes & fees
9/10 Wonderful! (699 reviews)
"Clean and super friendly staff. When the front desk informed me of the breakfast hours at check in I said I would be leaving very early before breakfast. He said if I got hungry in the night to let him know and he would open the breakfast room so I could have a snack. I thought that was very ..."

Reviewed on 10 Jul. 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 NZ$252 per night from 14 July to 15 July
NZ$252
14 July - 15 July
includes taxes & fees
9.2/10 Wonderful! (646 reviews)
"Lovely hotel on the edge of Winterset with large and airy rooms. Staff were friendly and helpful at all times. The constant supply of excellent coffee was great too. Easy parking. Thought it excellent value for money for a woman travelling alone!"

Reviewed on 7 Jul. 2025

Cobblestone Inn & Suites - Winterset, IA
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
The price is NZ$257 per night from 21 July to 22 July
NZ$257
21 July - 22 July
includes taxes & fees
9.4/10 Exceptional! (1,024 reviews)
"Bueno"

Reviewed on 12 Jul. 2025

Hotel Fort Des Moines, Curio Collection by Hilton
See all 521 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 holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday 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 holiday packages and you could land some great off-season discounts.
How many days is enough for Winterset?
The ideal length for your Winterset holiday depends on what you'd like to do and see. Usually, a few days to a week will give you time to visit all the main sights and discover some hidden spots along the way.
Is it worth booking a holiday package to Winterset?
Winterset is a good holiday destination with attractions like The Winterset Stage among the many things to keep you entertained. Whether you're travelling with the family or getting away with friends, a Winterset holiday promises a good time for everyone.
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 holiday package well in advance.
Is it cheaper to book a Winterset holiday as a package?
An Expedia holiday 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 holiday 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, favourite 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 accommodation 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 holiday package that brings all your bookings together.

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