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Find hotels in Winterset, IA from ₩84,392

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Our top choices for Winterset hotels

Porch
Covered Bridge Inn

Covered Bridge Inn

Covered Bridge Inn
2.5 star property
Winterset
9.0 out of 10, Wonderful, (768)
Serene retreat with complimentary breakfast, WiFi, and parking just minutes from the John Wayne Birthplace Museum. Clean rooms and helpful staff create a restful atmosphere, with The Winterset Stage nearby for entertainment.
"Breakfast was top notch for the price."
United States
Raymond
The price is ₩115,572
₩129,433 total
includes taxes & fees
Dec 16 - Dec 17
Covered Bridge Inn
Exterior
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)
Located near The Winterset Stage and John Wayne Birthplace Museum, this hotel offers a fitness center for active travelers. Enjoy a meal at the restaurant or relax with a drink at the bar after a day of sightseeing, plus free breakfast, WiFi and parking.
"Great place to stay. "
United States
Steve
The price is ₩159,578
₩178,729 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, (596)
"Nice location, good breakfast and helpful staff."
United States
Christopher
The price is ₩159,519
₩178,661 total
includes taxes & fees
Dec 26 - Dec 27
AmericInn by Wyndham Osceola
Bar (on property)
Lakeside Hotel Casino

Lakeside Hotel Casino

Lakeside Hotel Casino
3.0 star property
Osceola
8.2 out of 10, Very Good, (1003)
Escape to this Osceola retreat near Lakeside Casino with convenient train station access. The hotel offers free WiFi, complimentary parking, and a fitness center. After swimming laps, enjoy drinks at the bar or dine at the onsite restaurant.
"We had a great time "
United States
Todd
The price is ₩106,380
₩139,687 total
includes taxes & fees
Dec 16 - Dec 17
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)
Just minutes from the National Balloon Museum, this hotel offers an indoor pool for refreshing dips any time of year. Enjoy complimentary breakfast, WiFi, and parking while exploring local attractions. The fitness center provides additional recreational options.
"I stay at this property multiple times a year and have always had a positive experience. "
United States
John
The price is ₩162,031
₩181,476 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, (1162)
Located just minutes from Des Moines Airport, this hotel offers scheduled free shuttles and daily continental breakfast. Rooms include refrigerators and microwaves, while a 24-hour fitness center and snack bar provide added convenience for travelers.
"Great breakfast for the price point. Hotel front desk is very professional and Manager is very responsive and customer service focused. "
United States
Rob
The price is ₩121,837
₩136,457 total
includes taxes & fees
Dec 30 - Dec 31
Baymont by Wyndham Des Moines Airport
Indoor pool
Quality Inn Osceola

Quality Inn Osceola

Quality Inn Osceola
2.5 star property
Osceola
8.4 out of 10, Very Good, (61)
This ideally positioned hotel offers complimentary breakfast, WiFi, and parking. Guests appreciate the helpful staff and clean, quiet rooms. Take a refreshing swim in the indoor pool before exploring nearby attractions like Revelton Distilling Company.
"Great place to stay!!!"
United States
Cynthia
The price is ₩132,994
₩148,953 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Quality Inn Osceola
Property amenity
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)
Experience quiet comfort at this Clive hotel, where free breakfast, WiFi and parking await. Take a refreshing dip in the indoor pool after exploring nearby Jordan Creek Town Center. Travelers praise the helpful staff and convenient location.
"Great place to stay! "
United States
Kirsten
The price is ₩94,130
₩105,426 total
includes taxes & fees
Dec 30 - Dec 31
La Quinta Inn & Suites by Wyndham Des Moines West Clive
Lobby
Evergreen Inn

Evergreen Inn

Evergreen Inn
2.5 star property
Osceola
9.0 out of 10, Wonderful, (689)
Conveniently located near the train station, this welcoming motel offers complimentary WiFi and parking. Clean rooms provide a comfortable retreat after exploring nearby Osceola Public Library and Little Indian Park. The attentive staff ensures a pleasant experience.
"Wonderful staff, easy check in & out. Comfortable and Clean place to stay! "
United States
Richard
The price is ₩77,136
₩86,386 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, (1683)
Escape the bustle at this quiet Des Moines retreat, just 1 mile from the airport with 24-hour shuttle service. Dive into the indoor pool, enjoy free breakfast, and rest on comfortable beds. Convenient for Drake University visits and shopping excursions.
"Had a great stay and was impressed with the staff and the hotel. Will stay again!"
United States
Kevin
The price is ₩93,096
₩104,267 total
includes taxes & fees
Dec 21 - Dec 22
Days Inn & Suites by Wyndham Des Moines Airport
Terrace/patio
Hotel Pommier Indianola

Hotel Pommier Indianola

Hotel Pommier Indianola
2.5 star property
Indianola
9.2 out of 10, Wonderful, (431)
Discover a welcoming retreat in Indianola with convenient amenities including complimentary breakfast, WiFi, and parking. The 24-hour fitness center keeps your routine intact while the attentive staff ensures a pleasant stay near the National Balloon Museum and Buxton Park Arboretum.
"Everything was wonderful. "
United States
Garrett
The price is ₩110,592
₩123,862 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, (1003)
Quiet refuge with comfortable rooms near local attractions including Jordan Creek Town Center. Free breakfast, WiFi, and parking enhance your experience, while the indoor pool and fitness center offer relaxation. Helpful staff ensure a pleasant business or leisure visit.
"Passing through on way to Michigan from Colorado. Convenient location, excellent service, comfortable room, good breakfast. "
United States
Bennet
The price is ₩129,181
₩144,683 total
includes taxes & fees
Dec 21 - Dec 22
Fairfield Inn and Suites by Marriott Des Moines West
Indoor pool
AmericInn by Wyndham Stuart

AmericInn by Wyndham Stuart

AmericInn by Wyndham Stuart
2.5 star property
Stuart
8.4 out of 10, Very Good, (522)
Set in the heart of Stuart, this inviting hotel offers a refreshing indoor pool and complimentary daily continental breakfast. Guest rooms provide a clean, comfortable retreat after exploring the area, with free WiFi and parking enhancing your Iowa stay.
"Was clean and nice."
United States
Christopher
The price is ₩125,014
₩145,926 total
includes taxes & fees
Dec 22 - Dec 23
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, (709)
Located in West Des Moines, this motel offers clean rooms with 24-hour front desk service. Jordan Creek Town Center and Des Moines Golf & Country Club are nearby. Enjoy complimentary WiFi, free parking, and a snack bar/deli during your stay.
"Very clean friendly staff "
United States
Isaiah
The price is ₩75,348
₩84,392 total
includes taxes & fees
Dec 28 - Dec 29
Motel 6 West Des Moines, IA
Indoor pool
Quality Inn Indianola

Quality Inn Indianola

Quality Inn Indianola
2.5 star property
Indianola
7.6 out of 10, Good, (513)
Discover comfort at this welcoming hotel with an indoor pool for year-round swimming. Near National Balloon Museum and Indianola Country Club, guests enjoy complimentary WiFi, parking, and breakfast. Travelers consistently praise the helpful staff and clean accommodations.
"The staff was kind and the hotel rooms clean"
United States
Stephanie
The price is ₩99,731
₩111,699 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Quality Inn Indianola
1 bedroom, desk, blackout drapes, soundproofing
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)
This railway-adjacent motel offers complimentary continental breakfast, WiFi, and parking. Work out anytime in the 24-hour fitness center before exploring nearby Warren Family Park or Revelton Distilling Company. Guests consistently praise the attentive staff for their exceptional service.
"Very convenient location and wonderful staff!"
United States
Sandra
The price is ₩119,695
₩134,058 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)
Enjoy free perks including breakfast, WiFi and parking at this Norwalk hotel. Cool off in the seasonal outdoor pool after exploring nearby Echo Valley Driving Range or Willow Creek Golf Club. Just 21 minutes from Des Moines International Airport.
"We would stay there again"
United States
Mark
The price is ₩141,860
₩158,884 total
includes taxes & fees
Dec 18 - Dec 19
Fairfield by Marriott Inn & Suites Norwalk
Indoor pool, outdoor pool, sun loungers
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, (1797)
Unwind at this relaxing Iowa retreat near Merle Hay Mall. Featuring indoor and outdoor pools, hot tub, and fitness center. The comfortable rooms include refrigerators and microwaves, while free breakfast, WiFi and parking enhance your stay.
"The breakfast and coffee was absolutely amazing. "
United States
Brenda
The price is ₩144,352
₩161,674 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Stoney Creek Hotel Des Moines - Johnston
Indoor pool, outdoor pool
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, (1006)
Located 15 minutes from Jordan Creek Town Center, this West Des Moines hotel offers both indoor and outdoor pools plus a fitness center. Guests love the free breakfast, WiFi, parking, and exceptional service, with easy access to West Glen Town Center.
"The location was great."
United States
Sherri
The price is ₩147,756
₩165,489 total
includes taxes & fees
Dec 21 - Dec 22
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, (1001)
This business-friendly hotel offers free breakfast, WiFi, and parking just a 15-minute drive from Jordan Creek Town Center. The indoor pool invites morning swims, while the 24-hour fitness center keeps workout routines on track. Guests praise the clean rooms and helpful staff.
"Very clean, quiet and great staff"
United States
James
The price is ₩137,427
₩153,919 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 ₩75,348 per night from Dec 28 to Dec 29
₩75,348
₩84,392 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.
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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