Winterset vacation rentals

We found 10 vacation rentals — enter your dates for availability

Discover a selection of 6 homes and other vacation rentals in Winterset that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll find the amenities you need and want, which might include WiFi and a pool. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about Winterset

Why visit Winterset

  • Outdoor Adventures: Enjoy hiking and biking in Winterset's beautiful urban parks and scenic trails.
  • Historic Bridges: Discover the iconic covered bridges that are a hallmark of Winterset's history and charm.
  • Charming Neighborhoods: Stroll through the quaint Town Square and nearby areas filled with unique shops and local eateries.
  • Cozy Accommodations: Choose from a variety of vacation rentals, including charming cabins and private homes.
  • Rich Local Culture: Immerse yourself in the friendly atmosphere and explore Winterset's vibrant history.

Popular types of accommodation in Winterset

Winterset offers a variety of vacation rental options to suit every traveler’s needs. From cozy houses and charming cabins to convenient apartments, you'll find the perfect place to unwind. Whether you're looking for a winter getaway or an extended stay, our listings provide transparent pricing and a selection of rental choices in Winterset, IA. Explore the array of Winterset vacation rentals and discover the ideal home away from home for your next adventure.

  • Houses: These spacious and comfortable homes are the top choice for visitors seeking a cozy retreat in Winterset, perfect for families or groups.
  • Apartments: Ideal for solo travelers or couples, these well-equipped apartments provide a convenient and home-like atmosphere in the heart of Winterset.
  • Cabins: Rustic and charming, cabins offer a unique getaway experience surrounded by nature, making them a favorite for outdoor enthusiasts.
  • Condos: These modern accommodations blend comfort and convenience, appealing to those who prefer a more urban setting during their stay.
  • Villas: Luxurious and spacious, villas offer an upscale experience for travelers looking for comfort and elegance in Winterset.**

Top attractions in Winterset

Winterset, Iowa, is the perfect destination for outdoor enthusiasts, families, and couples alike. Explore its beautiful urban parks, historic bridges, and charming town neighborhoods. With a variety of attractions catering to both adventure seekers and those looking for a relaxing city experience, Winterset offers something for everyone. Make sure to discover the local points of interest that will make your vacation memorable.

  • John Wayne Birthplace Museum: Celebrate the legacy of the legendary actor at this museum dedicated to his life and career. Explore exhibits showcasing memorabilia and learn about his impact on American cinema in a charming, culturally rich environment.
  • Roseman Bridge: This historic bridge offers picturesque views and a glimpse into the past. Known for its unique architecture and romantic setting, it's a great spot for photos and exploring local history.
  • Madison County Courthouse: A stunning example of 19th-century architecture, this courthouse is a vibrant hub of community life. Enjoy its friendly atmosphere, trendy shops nearby, and family-friendly activities in the surrounding area.

Things to do recommended for couples

In Winterset, Iowa, couples can enjoy a romantic stroll through the beautiful Winterset City Park, explore the charming shops downtown, or visit the iconic John Wayne Birthplace Museum. Don’t miss a sunset picnic at the scenic Madison County Covered Bridges for an unforgettable experience together.

Things to do recommended for families

Families will love exploring the historic sites of Winterset, including the beautiful John Wayne Birthplace Museum and the scenic Madison County Covered Bridges. Enjoy a picnic at the Winterset City Park or take a family hike along the trails, creating lasting memories together.

Things to do recommended for groups

Groups visiting Winterset can enjoy a tour of the historic John Wayne Birthplace Museum, explore the picturesque bridges of Madison County, and savor local flavors at charming eateries. Don’t miss the scenic beauty at Winterset City Park for a delightful outdoor experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Winterset

If you're traveling with a group, with family, bringing your pets, or seeking longer stays, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winterset with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Winterset with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Winterset: For many families, a vacation wouldn’t be the same without their furry companions. If that resonates with you, consider exploring Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Winterset: If you're in search of vacation rentals offering discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Winterset

Winterset, Iowa, offers a delightful blend of outdoor adventures and charming local experiences, making it perfect for family, romantic, or solo getaways. Explore nearby neighborhoods like Van Meter and the historic Town Square, where quaint shops invite leisurely strolls. Immerse yourself in the friendly atmosphere and rich history that define this beautiful region, ensuring a memorable vacation filled with warmth and discovery.

  • East Peru: Located 9 miles from Winterset, East Peru is a charming city that offers a delightful blend of cultural and scenic experiences. Visitors are drawn to its rich history and picturesque surroundings, making it an ideal spot for a romantic getaway or a cultural excursion. The area boasts several notable landmarks, including a historic bridge and a monument that reflect its heritage. For those interested in educational experiences, East Peru provides opportunities to engage with local history and culture, enhancing your travel experience with a touch of learning amidst beautiful scenery.
  • Saint Charles: Just 11 miles from Winterset, Saint Charles is a vibrant city perfect for family outings and entertainment. The town features an arena entertainment facility and a shopping mall, offering a variety of activities for visitors of all ages. Outdoor enthusiasts will appreciate the nearby urban park and lake, ideal for leisurely strolls or picnics. Saint Charles is a great destination for those looking to blend shopping, recreational activities, and family fun in a welcoming environment.
  • Earlham: Situated 12 miles from Winterset, Earlham is renowned for its stunning outdoor scenery and romantic atmosphere. With a recreational area and golf course, it’s a fantastic spot for those looking to enjoy nature or engage in outdoor sports. The nearby national state park and urban park provide ample opportunities for hiking, picnicking, and soaking in the natural beauty of the landscape. Earlham is a perfect retreat for couples seeking a serene escape or anyone wanting to immerse themselves in the great outdoors.

Best time to go to Winterset

If you're planning a trip to Winterset, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like February and November to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.1°F (-5.5°C)No Rain (Dry)Mostly CloudyAverageSlightly Low
February24.6°F (-4.1°C)No Rain (Dry)Mostly SunnySlightly LowSlightly Low
March39.6°F (4.2°C)Light RainMostly CloudyAverageSlightly Low
April50.0°F (10.0°C)Light RainMostly SunnyAverageAverage
May61.0°F (16.1°C)Light RainMostly SunnyAverageAverage
June71.6°F (22.0°C)Light RainMostly SunnySlightly HighSlightly High
July74.8°F (23.8°C)Light RainMostly SunnySlightly HighSlightly High
August73.2°F (22.9°C)Light RainMostly SunnyAverageSlightly High
September66.7°F (19.3°C)Light RainMostly SunnySlightly HighAverage
October53.1°F (11.7°C)Light RainMostly SunnyAverageAverage
November40.5°F (4.7°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December29.3°F (-1.5°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental. We're here to help you find the best options for your trip.

Vrbo Trips: Planning made easy

Vrbo's Trip Board is designed to help you plan your journeys seamlessly. You can create new trips, pick up where you left off, or manage and organize your reservations. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Travel to friendly Winterset

Learn about the unique charm of Winterset with a stay in a private vacation home. This welcoming and trendy city is known for its shopping, restaurants and bars. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Winterset

Are you searching for things to do in the city? Venture out of your vacation home and experience everything that Winterset has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Des Moines Golf & Country Club (20.8 mi / 33.6 km)
  • Indianola Country Club (23.5 mi / 37.8 km)
  • Pump It Up (24.2 mi / 38.9 km)
  • Pammel State Park (4 mi / 6.4 km)
  • Willow Creek Golf Club (21 mi / 33.8 km)
  • Lake Ahquabi State Park (22.2 mi / 35.8 km)

Exploring the natural landscape of Winterset

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Winterset is a great place to get out in nature. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Raccoon River Valley Trail (20.1 mi / 32.3 km)
  • Brenton Arboretum (22.7 mi / 36.5 km)
  • Pammel State Park (4 mi / 6.4 km)
  • Van Meter Recreation Complex (14.5 mi / 23.3 km)
  • Lake Ahquabi State Park (22.2 mi / 35.8 km)
  • Brookshire Open Space (22.2 mi / 35.8 km)

Transportation options to and around Winterset

The nearest airport is in Des Moines International Airport (DSM), located 23.5 mi (37.9 km) from the city center.

Frequently asked questions

How much does it cost to rent a vacation home in Winterset?
Prices for vacation rentals in Winterset vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winterset to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winterset vacation house rentals?
You can find great discounts on house rentals in Winterset on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Winterset?
In Winterset, vacation houses are the most popular type of rental, with several available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also come with outdoor areas for relaxation, allowing guests to enjoy the beautiful surroundings. Additionally, there are several charming cottages and cabins available, offering a cozy and rustic atmosphere for those looking to escape and unwind.
Are there any family house rentals in Winterset?
In Winterset, Iowa, there are several family-friendly house rentals available, making it an excellent choice for groups looking to enjoy a family getaway. The area features spacious homes that often include amenities like full kitchens, cozy living areas, and outdoor spaces great for family activities.

Visitors can explore nearby attractions such as the famous Madison County Covered Bridges, which provide both scenic views and opportunities for outdoor adventures. Additionally, the town has lovely parks where families can enjoy picnics and recreational activities.
Can I find long-stay vacation rentals in Winterset?
A long-stay vacation rental in Winterset is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any remote work vacation rentals in Winterset?
In Winterset, Iowa, there are several remote work-friendly vacation rentals available, making it a suitable destination for those looking to combine work and leisure. Many properties come equipped with amenities such as free Wi-Fi in rooms, ensuring connectivity for remote work needs. Travelers can expect comfortable living spaces that may include dedicated work areas, allowing for productivity while enjoying the charming surroundings of this historic town. The picturesque countryside and access to local attractions like the famous John Wayne Birthplace Museum and the scenic Winterset City Park provide opportunities for relaxation after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winterset vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winterset with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winterset?
In Winterset, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many rentals also offer blenders for those who enjoy smoothies or soups, as well as coffee and tea makers for a warm beverage to start the day. Onsite parking is commonly available, providing convenience for travelers with vehicles. Additionally, many properties feature patios, where guests can relax outdoors and enjoy the peaceful surroundings of this charming Iowa town.
When is the best time to visit Winterset for a vacation rental?
The best time to visit Winterset for a vacation rental is during the peak season from July to September. This vibrant period draws visitors eager to explore the scenic beauty and rich history of the area, including the iconic covered bridges that inspired the novel "The Bridges of Madison County." With warm temperatures averaging in the mid-70s to mid-80s Fahrenheit, outdoor enthusiasts can enjoy a variety of activities such as hiking, biking, and sightseeing.

July, in particular, stands out as the most popular month, bustling with lively events and festivals that showcase local culture. Visitors can engage in the community atmosphere and indulge in the delightful offerings of local farmers' markets, art shows, and music festivals.

For those seeking a more budget-friendly option, consider planning your trip in December. While this month may offer cooler temperatures in the 30s to low 40s Fahrenheit, it presents a unique charm with festive holiday decorations and a quieter pace, superb for reflective strolls through the historic downtown area.
How early should I book a Winterset vacation rental?
Book your Winterset vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winterset, Iowa, United States of America?
In Winterset, visitors can explore several great attractions that highlight the town's rich history and natural beauty. The Madison County Courthouse, an iconic structure, is situated in the historic downtown area and is surrounded by charming shops and local eateries. Nearby, the Winterset City Park offers picturesque views and walking trails, making it a lovely spot for outdoor activities.

One of the most famous attractions in Winterset is the birthplace of John Wayne, which is located within a short distance from the downtown area. The museum dedicated to the legendary actor showcases his life and career, drawing fans from far and wide. Additionally, the Covered Bridges of Madison County, located just outside of Winterset, are a significant draw for visitors, offering stunning photo opportunities and a glimpse into the region's history.
Can I change or cancel my Winterset home rental booking on Vrbo?
To find Winterset vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winterset vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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