Winterset Vacations

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Find the Best Winterset Vacation Packages

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 ₩126,589 per night from Apr 17 to Apr 18
₩126,589
₩139,248 total
includes taxes & fees
Apr 17 - Apr 18
9/10 Wonderful! (668 reviews)
Clean and affordable
"It was clean and affordable. Staff was nice. The only issue we had was someone had a dog that kept constantly barking for hours. We knew the hotel accepted pets so it’s not their fault. Just an FYI for anyone booking. It’s an older hotel as well, which is fine with us. We had a nice stay and would ..."

Reviewed on Apr 14, 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 ₩140,798 per night from May 4 to May 5
₩140,798
₩157,696 total
includes taxes & fees
May 4 - May 5
9.2/10 Wonderful! (616 reviews)
"The check in person was excellent. Would recommend better pillows and an additional chair besides the office chair in the room. Would recommend this place to others."

Reviewed on Apr 8, 2025

Cobblestone Inn & Suites - Winterset, IA
Stoney Creek Hotel Des Moines - Johnston
Stoney Creek Hotel Des Moines - Johnston
2.5 out of 5
5291 Stoney Creek Court, Johnston, IA
Fully refundableReserve now, pay when you stay
The price is ₩155,001 per night from Apr 17 to Apr 18
₩155,001
₩173,601 total
includes taxes & fees
Apr 17 - Apr 18
8.8/10 Excellent! (1,653 reviews)
"The property is clean. I love the woodsy logged look. Smelled clean and the front desk staff was courteous. The room I had was spacious and even had a massage chair which believe me I took the liberty of using. It is very quiet. I didn't hear a peep. The main building has a pool and Sauna. You get ..."

Reviewed on Apr 15, 2025

Stoney Creek Hotel Des Moines - Johnston
See all 502 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 vacation package cost?
Offering great value package deals 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?
You’re likely to find lower rates and greater availability in December, January and February. Explore our cheap Winterset vacation packages and you could land some great off-season discounts.
How many days is enough for Winterset?
The ideal length for your Winterset vacation 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 vacation package to Winterset?
Winterset is a good vacation destination with attractions like The Winterset Stage among the many things to keep you entertained. Whether you’re traveling with the family or getting away with friends, a Winterset vacation 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 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.
How to plan a trip to Winterset?

  1. Choose the right time to travel: Your schedule, favorite 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 accommodations 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 vacation 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.