Find hotels in Winterset, IA from $62

These Winterset insights are based on real traveler data from Expedia, aggregated using AI to help you plan your trip. Updated: September 13, 2026.

Top reasons to visit Winterset

• Historic Bridges: Explore the picturesque historic bridges that dot the landscape, providing a glimpse into Winterset's rich history.
• Charming Shopping Center: Enjoy a leisurely day at local shops, showcasing the town's friendly atmosphere and unique offerings.
• Outdoor Adventures: Take advantage of beautiful parks and hiking trails, perfect for families and romantics alike.
• Welcoming Accommodations: Choose from a variety of cozy lodging options, including pet-friendly and LGBTQIA-friendly stays.
• Scenic Neighborhoods: Stroll through charming neighborhoods that reflect the town's inviting vibe and natural beauty.

Find great hotels near Winterset

Winterset, Iowa, offers a variety of accommodation options to suit every traveler, from cozy motels to welcoming hotels. Whether you're seeking a pet-friendly stay, a business-friendly environment, or an LGBTQIA-friendly experience, you'll find the perfect fit here. Notable options include the Cobblestone Inn, among the best hotels in the area. Explore the charm of Winterset while enjoying the comforts of your chosen lodging.

• Motel 6 West Des Moines, IA: A budget-friendly option located 21 miles from Winterset, Motel 6 West Des Moines, IA is perfect for travelers seeking a simple and economical stay. This motel embraces a pet-friendly philosophy, welcoming furry companions with open arms. Its amenities include no fees for service animals and a relaxed policy for pets, making it an ideal choice for those who want to travel with their pets without breaking the bank. Enjoy easy access to nearby attractions while keeping your budget intact.
• Hyatt Place West Des Moines Jordan Creek: Situated just 20 miles from Winterset, this 3-star hotel boasts a remarkable guest rating of 9.2. Hyatt Place West Des Moines Jordan Creek caters to both business travelers and vacationers with pets. The hotel features modern amenities, including spacious rooms and a business center, ensuring a comfortable stay for all guests. Its pet policy allows for pets with specific weight limits and fees, combining convenience with a welcoming atmosphere. Enjoy a blend of comfort and professionalism in a stylish setting.
• Sonesta Simply Suites Des Moines: Another budget-friendly choice located 21 miles from Winterset, Sonesta Simply Suites Des Moines offers a guest rating of 8.4. This hotel is tailored for those traveling with pets and business needs. With a relaxed pet policy that includes fees and restrictions, it provides a welcoming environment for both you and your furry friends. The hotel features essential amenities like a fitness center and laundry facilities, ensuring a practical and comfortable stay for all types of travelers. Experience home-like comforts while on the road.

Where to stay near Winterset

Winterset, Iowa, offers a charming escape for families and couples alike. Explore local shops that reflect the town's friendly atmosphere, or enjoy romantic getaways surrounded by scenic spots. The area boasts a warm, inviting vibe, perfect for outdoor adventures, whether you're hiking the trails or relaxing in parks. Don't miss the historical sites that add a unique touch to your visit, making Winterset a delightful destination for all types of travelers.

• Patterson: Nestled a mere 7 miles from Winterset, Patterson is a quaint city that offers a delightful escape for outdoor enthusiasts and families alike. The area's recreational spaces are perfect for picnics and leisurely strolls, especially during the summer months from June to August, when visitor numbers peak. Notable highlights include the urban park and nearby lake, which provide opportunities for fishing, hiking, and enjoying nature. While the town sees fewer visitors in the winter, it maintains a charming, small-town ambiance year-round.
• East Peru: Located 9 miles from Winterset, East Peru is a city that captures the essence of culture and romance. Travelers flock here for scenic views and educational experiences, making it an ideal destination for couples and culture enthusiasts. The city’s historic bridge and monuments are must-see attractions, with the best time to visit being during the summer months when the weather is pleasant. Despite lower visitor numbers in winter, East Peru's rich history and picturesque surroundings make it a charming stop on your journey.
• Saint Charles: Situated 11 miles from Winterset, Saint Charles is a vibrant city that offers a mix of family-friendly activities and entertainment. The city experiences peak tourism in February and from June to July, with visitors drawn to its shopping centers and arena entertainment facilities. Nearby attractions like the event conference venue, lake, and urban parks provide ample opportunities for relaxation and outdoor fun. Although it sees fewer visitors from October to December, Saint Charles remains a lively hub worth exploring during your vacation.

Things to do near Winterset

Winterset, Iowa, offers a delightful blend of outdoor adventures and family-friendly activities, perfect for romantic getaways or family vacations. Explore the charming shopping center and recreational areas while discovering the treasures that Winterset has to offer. Whether you’re looking for a leisurely day of shopping or an exciting outdoor experience, Winterset presents a variety of attractions for every visitor.

Shopping

In Winterset, you can explore local shops like the Winterset Marketplace for unique gifts and handcrafted items. If you're up for a drive, head to the nearby Jordan Creek Town Center, where you'll find a variety of retail stores and dining options to enhance your shopping experience.

Recreation

Experience the luxurious atmosphere at Osceola Country Club, located 25 miles from Winterset. Enjoy a round of golf on beautifully manicured greens, unwind with spa treatments, and savor delicious meals in their elegant dining area for a perfect wellness escape.

Adventure

Explore the scenic trails at Winterset City Park, perfect for hiking and picnicking amidst beautiful landscapes. For a thrilling experience, try zip-lining at the nearby Adventure Park, where you can soar above the trees and feel the rush of adrenaline in a stunning natural setting.

Nightlife

Experience the cozy ambiance at The Brick City Grill, where you can enjoy hearty meals and local brews. For a lively night, check out the Winterset Community Theatre for a show, or unwind with friends at the Madison County Winery for wine tasting and stunning views.

Booking tips and Expedia advantages for Winterset

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winterset are November to January, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winterset is Monday. The most expensive day to stay in Winterset is Saturday.
• Find cheap hotels on Expedia: Utilize Expedia’s search tool to refine your options based on your budget, desired location, and preferred type of accommodation. To find the best prices and offers, arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by booking an Expedia package that combines your Winterset hotel with your flights and activities.

Find the best attractions in Winterset

Winterset, Iowa, is perfect for outdoor, family, and romantic getaways. Visitors can explore popular attractions like urban parks, historic bridges, and charming town neighborhoods. This quaint destination offers a blend of outdoor activities and city experiences, making it an ideal spot for travelers seeking to enjoy the natural beauty and rich history of the area.

• John Wayne Birthplace Museum: Discover the life and legacy of the legendary actor John Wayne at this charming museum located in his hometown. Explore exhibits filled with photographs, memorabilia, and interactive displays that showcase his contributions to film and American culture.
• Roseman Bridge: Experience the historic charm of Roseman Bridge, a picturesque covered bridge that embodies the essence of Madison County. Known for its stunning architecture and scenic surroundings, it’s a perfect spot for photography and a leisurely stroll.
• Madison County Courthouse: Visit the grand Madison County Courthouse, a stunning example of Richardsonian Romanesque architecture. This vibrant hub offers a friendly atmosphere, ideal for families and visitors looking to relax while exploring local history.

Best time to go to Winterset

The best time to visit Winterset can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winterset falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winterset falls in January, visitor numbers are average and weather is mostly cloudy with no rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	22.1°F (-5.5°C)	No Rain	Mostly Cloudy	Average	Slightly Low
February	24.6°F (-4.1°C)	No Rain	Mostly Sunny	Slightly Low	Average
March	39.6°F (4.2°C)	Light Rain	Mostly Cloudy	Average	Average
April	50.0°F (10.0°C)	Light Rain	Mostly Sunny	Average	Average
May	61.0°F (16.1°C)	Light Rain	Mostly Sunny	Average	Average
June	71.6°F (22.0°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	74.8°F (23.8°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	73.2°F (22.9°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	66.7°F (19.3°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	53.1°F (11.7°C)	Light Rain	Mostly Sunny	Average	Average
November	40.5°F (4.7°C)	No Rain	Mostly Sunny	Slightly Low	Slightly Low
December	29.3°F (-1.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

The nearest major airports for your trip to Winterset

To visit Winterset, Iowa, you have several airport options. Des Moines International Airport (DSM) is the closest, located 24 miles away, with nearby hotels like the 4.5-star Hotel Fort Des Moines, just 4 miles from the airport. OMAha's Eppley Field (OMA) is 98 miles away, with comfortable stays like the 4.5-star Magnolia Hotel Omaha, only 4 miles from the airport. Fort Dodge Regional Airport (FOD), situated 85 miles from Winterset, offers hotel choices such as the Cobblestone Inn & Suites, located 4 miles from the airport. Each hotel provides convenient access to their respective airports, ensuring a smooth travel experience.