Find hotels in Winterset, IA from ￥8,899

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Dec 14 - Dec 15
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Our top choices for Winterset hotels

Free daily continental breakfast
Covered Bridge Inn

Covered Bridge Inn

Covered Bridge Inn
2.5 star property
Winterset
9.0 out of 10, Wonderful, (768)
"Breakfast was top notch for the price."
United States
Raymond
The price is ￥12,186
￥13,647 total
includes taxes & fees
Dec 15 - Dec 16
Covered Bridge Inn
Lobby
Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA
2.5 star property
Winterset
9.2 out of 10, Wonderful, (712)
"Great place to stay. "
United States
Steve
The price is ￥16,826
￥18,846 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cobblestone Inn & Suites - Winterset, IA
Exterior
AmericInn by Wyndham Osceola

AmericInn by Wyndham Osceola

AmericInn by Wyndham Osceola
2.5 star property
Osceola
8.8 out of 10, Excellent, (595)
"Nice location, good breakfast and helpful staff."
United States
Christopher
The price is ￥16,820
￥18,838 total
includes taxes & fees
Dec 26 - Dec 27
AmericInn by Wyndham Osceola
Restaurant
Lakeside Hotel Casino

Lakeside Hotel Casino

Lakeside Hotel Casino
3.0 star property
Osceola
8.2 out of 10, Very Good, (1002)
"We had a great time "
United States
Todd
The price is ￥10,095
￥13,473 total
includes taxes & fees
Dec 22 - Dec 23
Lakeside Hotel Casino
Property amenity
Country Inn & Suites by Radisson, Indianola, IA

Country Inn & Suites by Radisson, Indianola, IA

Country Inn & Suites by Radisson, Indianola, IA
2.5 star property
Indianola
9.0 out of 10, Wonderful, (711)
"I stay at this property multiple times a year and have always had a positive experience. "
United States
John
The price is ￥17,085
￥19,135 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Country Inn & Suites by Radisson, Indianola, IA
Lobby
Baymont by Wyndham Des Moines Airport

Baymont by Wyndham Des Moines Airport

Baymont by Wyndham Des Moines Airport
2.5 star property
Southwestern Hills
9.4 out of 10, Exceptional, (1161)
"Friendly staff, quiet location, comfortable and clean rooms. Would stay there again."
United States
Alaina
The price is ￥12,847
￥14,389 total
includes taxes & fees
Dec 30 - Dec 31
Baymont by Wyndham Des Moines Airport
Desk, laptop workspace, soundproofing, iron/ironing board
Quality Inn Osceola

Quality Inn Osceola

Quality Inn Osceola
2.5 star property
Osceola
8.4 out of 10, Very Good, (61)
"Great place to stay!!!"
United States
Cynthia
The price is ￥14,023
￥15,706 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Quality Inn Osceola
Lobby
La Quinta Inn & Suites by Wyndham Des Moines West Clive

La Quinta Inn & Suites by Wyndham Des Moines West Clive

La Quinta Inn & Suites by Wyndham Des Moines West Clive
3.0 star property
Clive
8.6 out of 10, Excellent, (1002)
"Great place to stay! "
United States
Kirsten
The price is ￥9,925
￥11,116 total
includes taxes & fees
Dec 29 - Dec 30
La Quinta Inn & Suites by Wyndham Des Moines West Clive
Front of property
Evergreen Inn

Evergreen Inn

Evergreen Inn
2.5 star property
Osceola
9.0 out of 10, Wonderful, (688)
"Wonderful staff, easy check in & out. Comfortable and Clean place to stay! "
United States
Richard
The price is ￥8,133
￥9,108 total
includes taxes & fees
Dec 20 - Dec 21
Evergreen Inn
Exterior
Days Inn & Suites by Wyndham Des Moines Airport

Days Inn & Suites by Wyndham Des Moines Airport

Days Inn & Suites by Wyndham Des Moines Airport
2.0 star property
Greater South Side
8.6 out of 10, Excellent, (1682)
"Had a great stay and was impressed with the staff and the hotel. Will stay again!"
United States
Kevin
The price is ￥9,816
￥10,995 total
includes taxes & fees
Dec 21 - Dec 22
Days Inn & Suites by Wyndham Des Moines Airport
Free daily buffet breakfast
Hotel Pommier Indianola

Hotel Pommier Indianola

Hotel Pommier Indianola
2.5 star property
Indianola
9.2 out of 10, Wonderful, (431)
"Everything was wonderful. "
United States
Garrett
The price is ￥11,661
￥13,060 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hotel Pommier Indianola
Lobby
Fairfield Inn and Suites by Marriott Des Moines West

Fairfield Inn and Suites by Marriott Des Moines West

Fairfield Inn and Suites by Marriott Des Moines West
2.5 star property
West Des Moines
9.0 out of 10, Wonderful, (1002)
"Passing through on way to Michigan from Colorado. Convenient location, excellent service, comfortable room, good breakfast. "
United States
Bennet
The price is ￥13,621
￥15,256 total
includes taxes & fees
Dec 21 - Dec 22
Fairfield Inn and Suites by Marriott Des Moines West
Exterior
AmericInn by Wyndham Stuart

AmericInn by Wyndham Stuart

AmericInn by Wyndham Stuart
2.5 star property
Stuart
8.4 out of 10, Very Good, (520)
"Was clean and nice."
United States
Christopher
The price is ￥12,480
￥14,601 total
includes taxes & fees
Dec 21 - Dec 22
AmericInn by Wyndham Stuart
Free WiFi, bed sheets
Motel 6 West Des Moines, IA

Motel 6 West Des Moines, IA

Motel 6 West Des Moines, IA
2.0 star property
West Des Moines
7.8 out of 10, Good, (708)
"Very clean friendly staff "
United States
Isaiah
The price is ￥7,945
￥8,899 total
includes taxes & fees
Dec 28 - Dec 29
Motel 6 West Des Moines, IA
Free daily continental breakfast
Quality Inn Indianola

Quality Inn Indianola

Quality Inn Indianola
2.5 star property
Indianola
7.6 out of 10, Good, (513)
"The staff was kind and the hotel rooms clean"
United States
Stephanie
The price is ￥10,383
￥11,629 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Quality Inn Indianola
Lobby
Super 8 by Wyndham Osceola IA

Super 8 by Wyndham Osceola IA

Super 8 by Wyndham Osceola IA
2.0 star property
Osceola
8.6 out of 10, Excellent, (233)
"Very convenient location and wonderful staff!"
United States
Sandra
The price is ￥12,621
￥14,135 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Super 8 by Wyndham Osceola IA
Property amenity
Fairfield by Marriott Inn & Suites Norwalk

Fairfield by Marriott Inn & Suites Norwalk

Fairfield by Marriott Inn & Suites Norwalk
3.0 star property
Norwalk
9.4 out of 10, Exceptional, (72)
"We would stay there again"
United States
Mark
The price is ￥14,958
￥16,753 total
includes taxes & fees
Dec 17 - Dec 18
Fairfield by Marriott Inn & Suites Norwalk
Indoor spa tub
Stoney Creek Hotel Des Moines - Johnston

Stoney Creek Hotel Des Moines - Johnston

Stoney Creek Hotel Des Moines - Johnston
2.5 star property
Johnston
8.8 out of 10, Excellent, (1796)
"The breakfast and coffee was absolutely amazing. "
United States
Brenda
The price is ￥15,221
￥17,048 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Stoney Creek Hotel Des Moines - Johnston
Free daily buffet breakfast
Drury Inn & Suites West Des Moines

Drury Inn & Suites West Des Moines

Drury Inn & Suites West Des Moines
3.0 star property
West Des Moines
9.4 out of 10, Exceptional, (1005)
"Great place! "
United States
Michele
The price is ￥15,579
￥17,449 total
includes taxes & fees
Dec 18 - Dec 19
Drury Inn & Suites West Des Moines
Exterior
Holiday Inn Express & Suites West Des Moines - Jordan Creek by IHG

Holiday Inn Express & Suites West Des Moines - Jordan Creek by IHG

Holiday Inn Express & Suites West Des Moines - Jordan Creek by IHG
2.5 star property
West Des Moines
9.2 out of 10, Wonderful, (1000)
"Very clean, quiet and great staff"
United States
James
The price is ￥14,490
￥16,229 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express & Suites West Des Moines - Jordan Creek by IHG
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.
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Stay near popular Winterset attractions

An Old Red Covered Bridge Over A River

Roseman Bridge

4.7/5 (35 reviews)
This 1883 wooden bridge gained fame in "The Bridges of Madison County" film with its distinctive flat roof and lattice design. Visit during autumn when vibrant foliage creates a perfect backdrop for photography.
See properties
An Old Red Covered Bridge

Holliwell Bridge

4.7/5 (29 reviews)
The longest covered bridge in Madison County, this historic 1880 structure gained fame in "The Bridges of Madison County." Walk through its timber lattice truss design while enjoying serene views of the Middle River.
See properties

Learn more about Winterset

Covered bridges beckon you to explore Madison County's scenic countryside, where John Wayne's birthplace museum awaits. Stroll the quaint town square, chatting with friendly locals over coffee before browsing antique shops brimming with treasures.

See all hotels in Winterset
hogback covered bridge, summer

Top Winterset Hotel Reviews

AmericInn by Wyndham Des Moines Airport

AmericInn by Wyndham Des Moines Airport

10/10 Excellent
"Room was clean enough "
Vilay 2-night trip
Posted 2 days ago
AmericInn by Wyndham Des Moines Airport

More cheap stays in Winterset

Motel 6 West Des Moines, IA

Motel 6 West Des Moines, IA

7655 Office Plaza Dr N West Des Moines IA
The price is ￥7,945 per night from Dec 28 to Dec 29
￥7,945
￥8,899 total
Dec 28 - Dec 29
includes taxes & fees
7.8/10 Good! (702 reviews)

Frequently asked questions

Where is the best place for a stay in Winterset?
Cobblestone Inn & Suites - Winterset, IA is a favorite with Expedia customers. This hotel offers free breakfast and a restaurant. Covered Bridge Inn is another top choice for your trip based on reviews. See all available top hotels, or vacation rentals in Winterset.
What are some of the best vacation rentals in Winterset?
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!: This vacation home rental near Winterset offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. See all vacation rentals in Winterset.
If I need to cancel my hotel reservation in Winterset, will I receive a refund?
Yes! Most hotel reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you have a reservation that's non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winterset.
Where can I learn more about changing or cancelling my trip to Winterset?
For more details about updating your trip to Winterset or cancelling it, click here.
What's the best pet-friendly accommodation in Winterset?
Cobblestone Inn & Suites - Winterset, IA is a top dog-friendly hotel, and offers a restaurant along with free WiFi for its human guests. Covered Bridge Inn is another option for you and your pet. See more pet-friendly hotel accommodations in Winterset.
Where is the best hotel to stay with easy access to Madison County Courthouse?
Cobblestone Inn & Suites - Winterset, IA is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and a restaurant. It's located just a short 0.8 mi (1.3 km) from Madison County Courthouse. Another good option is Covered Bridge Inn, located just 1 mi (1.5 km) away.
What about the best place to stay close to John Wayne Birthplace Museum?
One of the top choices for your stay is Cobblestone Inn & Suites - Winterset, IA, located a short 1 mi (1.6 km) from John Wayne Birthplace Museum, and this hotel offers free breakfast and a restaurant. Covered Bridge Inn, located 1 mi (1.6 km) away, is another good choice for your stay.
What are some accommodations with pools in Winterset?
Home2 Suites by Hilton Des Moines at Drake University: Hotel located near Casey's Center. Features buffet, an indoor pool, and complimentary wired internet access. Stoney Creek Hotel Des Moines - Johnston and Days Inn & Suites by Wyndham Des Moines Airport are two additional hotels with an onsite pool. View all hotels with pools in Winterset.
What is the best accommodation for staying close to Des Moines International Airport (DSM)?
Days Inn & Suites by Wyndham Des Moines Airport is a popular hotel, featuring free breakfast and an indoor pool. It's located a short 0.5 mi (0.7 km) from Des Moines Intl. Airport. Other good options near the airport are Ramada by Wyndham Des Moines Airport and Hampton Inn Des Moines Airport.
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 12 hotels and other accommodations to choose from. Find out more about Winterset.
What should I do while I'm visiting Winterset?
Cultural venues include John Wayne Birthplace Museum and The Winterset Stage. Landmarks like Clark Tower, Roseman Bridge, and Cedar Bridge might be worth a visit. A couple of additional sights to add to your agenda are Pammel State Park and Hogback Bridge. Check out what more 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 temp of 72°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Winterset are January, February, November, and March, with each month seeing an average of 9 inches of snowfall.

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