Winterset Holidays

Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀
    deals illustration
    Better together
    Save up to S$134 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Winterset

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 S$125 per night from 13 Jul to 14 Jul
S$125
13 Jul - 14 Jul
includes taxes & fees
9/10 Wonderful! (696 reviews)
"Breakfast was good. Not a fan of the condiments like the butter being a shared tub that everyone stuck the knife into. If you don't know how the Waffle maker works and how much batter to put in. You will struggle with this. But overall a very nice place to stay."

Reviewed on 30 Jun, 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 S$187 per night from 13 Jul to 14 Jul
S$187
13 Jul - 14 Jul
includes taxes & fees
9.2/10 Wonderful! (645 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 S$196 per night from 21 Jul to 22 Jul
S$196
21 Jul - 22 Jul
includes taxes & fees
9.4/10 Exceptional! (1,008 reviews)
"Excellent and professionnel staff"

Reviewed on 5 Jul, 2025

Hotel Fort Des Moines, Curio Collection by Hilton
See all 520 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.