Winterset, IA

Travel Guide

A red covered bridge over a calm river, surrounded by lush greenery and trees.
A red covered bridge over a river, surrounded by greenery and trees.
A red covered bridge with a white fence in a grassy field surrounded by trees.
A red covered bridge over a river, surrounded by greenery and a dirt path.
A red covered bridge with a white fence in the background.
Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA

2.5 out of 5
1304 North 4th Avenue Winterset IA
$108 nightly
The price is $121 total per night from Nov 8 to Nov 9
$121 total
Nov 8 - Nov 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Winterset. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (837 reviews)
"Great Hotel in Winterset! Everything you usually find in an excellent hotel provided! In addition they have a drop in food and Cocktail service in the dining room in addition to a wonderful free breakfast!!"

Reviewed on Nov 4, 2026

Cobblestone Inn & Suites - Winterset, IA
Covered Bridge Inn

Covered Bridge Inn

2.5 out of 5
1312 Cedar Bridge Rd. Winterset IA
$100 nightly
The price is $112 total per night from Nov 22 to Nov 23
$112 total
Nov 22 - Nov 23
Total with taxes and fees
Stay at this motel in Winterset. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Covered Bridge Inn
Hotel Fort Des Moines, Curio Collection by Hilton

Hotel Fort Des Moines, Curio Collection by Hilton

4.5 out of 5
1000 Walnut St Des Moines IA
$125 nightly
The price is $140 total per night from Nov 15 to Nov 16
$140 total
Nov 15 - Nov 16
Total with taxes and fees
Book a stay at this luxury hotel in Des Moines. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (1,410 reviews)
"Great experience! Love the speakeasy in the basement"

Reviewed on Nov 4, 2026

Hotel Fort Des Moines, Curio Collection by Hilton
See all 533 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.
The Little Brick House - Walkable to the Square Dining & Shopping

The Little Brick House - Walkable to the Square Dining & Shopping

Winterset IA
Stay at this vacation home in Winterset. Enjoy laundry facilities and air conditioning. Popular attractions John Wayne Birthplace Museum and The Winterset Stage ...
10/10 Exceptional! (23 reviews)
"What an adorable, clean, well kept and decorated little place! In a nice, quiet neighborhood! Host was great with communication! We really enjoyed our stay in Winterset, IA.Highly recommend this place if your going to see the bridges in Madison Co. Very convenient to everything! Thank you!"

Reviewed on Oct 28, 2026

The Little Brick House - Walkable to the Square Dining & Shopping
Modern home on acreage with pond, trails, rolling hills, and sunset views

Modern home on acreage with pond, trails, rolling hills, and sunset views

Winterset IA
Stay at this vacation home in Winterset. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Cedar Bridge and Clark Tower are located ...
10/10 Exceptional! (13 reviews)
"This was the perfect place for a girls getaway to see the bridges of Madison County. The house has a great kitchen, stocked with all the things you need to cook and eat. There is plenty of space to sit back and watch the Roku TV. The dining table is large and provided us a place to the play games ..."

Reviewed on Oct 25, 2026

Modern home on acreage with pond, trails, rolling hills, and sunset views
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Winterset IA
Stay at this vacation home in Winterset. Enjoy laundry facilities and air conditioning. Popular attractions The Winterset Stage and John Wayne Birthplace Museum ...
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
See all 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.

Stay near popular Winterset attractions

A red bridge over a calm river with greenery around.

Roseman Bridge

9.6/10 (75 reviews)
You can learn about the history of Winterset with a stop at Roseman Bridge. Make some time to visit the monuments while you're in the area.
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Frequently asked questions

Is Winterset worth visiting?
Winterset is worth visiting for its unique attractions, including the John Wayne Birthplace Museum and the historic Roseman Bridge. Travelers can also enjoy a range of dining experiences, with local North American and Italian cuisine available.
When is the best time to visit Winterset?
The best time to visit Winterset is from May through September, when the weather is generally pleasant. For travelers seeking fewer crowds and better value, the quieter months of December through March are a good option, offering a different experience during the cooler season.
What is Winterset known for?
Winterset is known for the John Wayne Birthplace Museum, celebrating the iconic actor. Travelers can also explore its historic covered bridges, including Roseman Bridge and Cedar Bridge, all within this riverside city.
What is a good itinerary length for Winterset?
A good itinerary length for Winterset is one to two days to visit key attractions like the John Wayne Birthplace Museum, Roseman Bridge, and Cedar Bridge. An extended stay of three to four days allows for a more relaxed pace, giving you extra time to explore the area and enjoy local dining, with options ranging from North American to Italian and Asian cuisine.
What are the top things to do in and around Winterset?
Winterset offers travelers a chance to explore historic landmarks and picturesque covered bridges:


How do I plan a trip to Winterset?
To plan your trip to Winterset, book hotels, flights, and rental cars in advance. You can also pre-book activities like visiting the John Wayne Birthplace Museum, Roseman Bridge, and Cedar Bridge. For outdoor plans, always have indoor backups ready for weather flexibility, ensuring a smooth and enjoyable visit.
What cuisines can you find in Winterset?
In Winterset you can find North American cuisine, with popular choices like burgers, steaks, and comforting macaroni and cheese. Travelers can also enjoy Italian dishes such as pasta, Asian flavors like stir-fries, and Latin American options including tacos.
Can I book a refundable hotel in Winterset?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Winterset by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Winterset with Expedia?
Expedia makes it easier to plan your Winterset trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Winterset?
The best choice depends on your travel style. Hotels in Winterset can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Winterset trip on Expedia?
Once you've booked your Winterset trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Winterset trip?
Expedia offers customer support before, during, and after your Winterset trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Winterset?
If it's your first trip to Winterset, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Winterset hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Winterset hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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A calm lake surrounded by trees and a cloudy sky.

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