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May 12 - May 13
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May 13 - May 14
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May 17 - May 19

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Top hotels and accommodation in Winterset

Covered Bridge Inn
Property entrance
Covered Bridge Inn
2.5 star property
9.4 out of 10, Exceptional, (567)
"."
The price is NZ$163
per night
24 May - 25 May
Covered Bridge Inn
Cobblestone Inn & Suites - Winterset, IA
Lobby
Cobblestone Inn & Suites - Winterset, IA
2.5 star property
9.2 out of 10, Wonderful, (525)
"Love Cobblestone properties because newer chain hotel and this stay didn’t disappoint!"
The price is NZ$189
per night
27 May - 28 May
Cobblestone Inn & Suites - Winterset, IA
Entire farmhouse in the country
Fridge, microwave, oven, stovetop
Entire farmhouse in the country
10.0 out of 10, Exceptional, (19)
"This home is warm and welcoming. Worked so well for a quick weekend away for us. Highly recommend."
Entire farmhouse in the country
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The Roost at Speckled Hen Farms.
Property grounds
The Roost at Speckled Hen Farms.
10.0 out of 10, Exceptional, (13)
"This is a great property in a picturesque setting. The decor was beautiful and the house was well stocked. The hosts were amazing and very responsive. They gave us great suggestions for restaurants and activities. We would definitely stay here again."
The Roost at Speckled Hen Farms.
St Charles 'Hilltop Mansion' w/ Mod Interior!
Fridge, microwave, stovetop, dishwasher
St Charles 'Hilltop Mansion' w/ Mod Interior!
St Charles 'Hilltop Mansion' w/ Mod Interior!
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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

If I need to cancel my hotel reservation in Winterset, will I receive a refund?

Yes! The majority of hotel reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a reservation that's non-refundable, you may still be able to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winterset.

What is staying in Winterset like?

Visitors can enjoy all that Winterset has to offer, including the shopping, restaurants and bars. The welcoming and quaint setting also entices those visiting the city. In Winterset, there are 10 hotels and other accommodation options to choose from. Find out more about Winterset.

What should I see while I'm in Winterset?

Cultural venues include John Wayne Birthplace Museum and The Winterset Stage. Landmarks like Roseman Bridge, Clark Tower and Cedar Bridge might be worth a visit. A couple of additional sights to add to your itinerary are Madison County Courthouse and Holliwell Bridge. Take a look at what more there is to see and do in Expedia's Winterset guide.

What's the seasonal weather like in Winterset?

The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winterset are January, February, November and April, with each month seeing an average of 22 cm of snowfall.