Winterset holiday rentals

We found 9 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Winterset that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the amenities that you expect and more, such as parking and air conditioning. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Travel to friendly Winterset

Learn about the unique charm of Winterset with a stay in a holiday home rental. This welcoming and trendy city is well known for its shopping, restaurants and bars. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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

Do you want to find things to do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Winterset a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Lake Ahquabi State Park (22.2 mi / 35.8 km)
  • Willow Creek Golf Club (21 mi / 33.8 km)
  • Clive Aquatic Center (22.8 mi / 36.8 km)
  • Indianola Country Club (23.5 mi / 37.8 km)
  • A. H. Blank Golf Course (23.7 mi / 38.2 km)
  • Pammel State Park (4 mi / 6.4 km)

Exploring the natural landscape of Winterset

Whether you're looking for fun outdoor activities or just want to take in the scenery, Winterset is a great place to get outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Raccoon River Valley Trail (20.1 mi / 32.3 km)
  • Lake Ahquabi State Park (22.2 mi / 35.8 km)
  • McKinley Park (27.3 mi / 43.9 km)
  • Pammel State Park (4 mi / 6.4 km)
  • Van Meter Recreation Complex (14.5 mi / 23.3 km)
  • Trailside Dog Park (20.9 mi / 33.7 km)

Transport 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 centre.

Frequently asked questions

What is the best area to stay in Winterset when booking a holiday rental?
When considering a holiday rental in Winterset, Iowa, a popular area to stay is near the historic downtown district. This charming neighbourhood offers a delightful blend of local shops, cafes, and restaurants, providing a vibrant setting for visitors. You'll find a variety of properties available here, ranging from cosy cottages to more spacious homes, suiting different group sizes and preferences.Staying in this area places you within easy reach of great attractions, such as the iconic John Wayne Birthplace Museum, which celebrates the life and legacy of the legendary actor. Additionally, the scenic Winterset City Park, known for its picturesque landscapes and walking trails, is nearby, making it superb for leisurely strolls or picnics.
What is the most popular type of holiday rental accomodation in Winterset?
In Winterset, holiday houses are the most popular type of holiday rental, with around 15 available throughout the area. These properties generally feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them suitable for families or groups seeking a comfortable home away from home. Additionally, several cottages and cabins can be found, offering a charming and rustic experience for those wishing to immerse themselves in the natural beauty of the region. These smaller rentals often boast picturesque settings and cozy interiors, ideal for a peaceful getaway.
Are there any family house rentals in Winterset?
In Winterset, Iowa, there are several family-friendly house rentals available, making it a great spot for families seeking a memorable getaway. The town is well-known for its picturesque surroundings and historical significance, including the famous John Wayne Birthplace Museum. Many of these homes boast spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play. Amenities like Wi-Fi and laundry facilities are common, ensuring a comfortable stay for all.Families can also enjoy nearby attractions, such as the charming Winterset City Park, which features playgrounds and scenic picnic spots.
Are there any remote work holiday rentals in Winterset?
In Winterset, Iowa, there are numerous options for remote work-friendly holiday rentals, with around 24 properties available. This charming town, known for its picturesque landscapes and historical significance, provides a conducive environment for those looking to blend work and leisure. Many of the rentals come equipped with essential amenities such as free Wi-Fi, dedicated workspaces, and desks, ensuring a comfortable setup for productivity.In addition to the practical work facilities, travellers can also enjoy the local attractions, such as the famous Bridges of Madison County and the scenic parks that offer opportunities for relaxation after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Winterset?
In Winterset, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals conveniently. Many rentals also feature blenders for those who enjoy making smoothies or other blended beverages. Onsite parking is commonly available, making it easy for travellers to access their accommodations without hassle. Additionally, many properties boast patios, providing a pleasant outdoor space to relax and enjoy the surroundings.
When is the best time to visit Winterset for a holiday rental?
The peak travel season in Winterset runs from July to September, attracting visitors eager to experience the vibrant summer atmosphere and the beautiful landscapes of Iowa. July, in particular, is the most popular month, where you can find a range of outdoor activities, including exploring the picturesque parks and enjoying the charming local events. The warm temperatures, typically ranging from 20 to 30 degrees Celsius, create ideal conditions for sightseeing and leisurely strolls through the town.During this lively time, you'll also have the chance to immerse yourself in Winterset's rich cultural heritage, including visits to the famous Covered Bridges and the John Wayne Birthplace Museum. The long summer days provide ample opportunity to enjoy these attractions, making it a fantastic choice for travellers.If you're looking for a more budget-friendly option, consider visiting in December. This month offers a unique charm with its festive decorations and quieter atmosphere, making it a great time for those who prefer a peaceful retreat. You can enjoy the beauty of Winterset without the hustle and bustle of the peak season, while still experiencing the warmth of the local community.Ultimately, your ideal time to visit Winterset will depend on whether you seek the vibrant energy of summer adventures or the serene beauty of wintertime exploration.
What are the top attractions in Winterset?
In Winterset, Iowa, visitors can enjoy a variety of attractions that highlight the town's rich history and natural beauty. The Madison County Courthouse, a stunning example of Victorian architecture, stands prominently in the town square and is a great starting point for exploring the area. Just a short distance away, the Winterset City Park offers picturesque landscapes, walking trails, and a lovely pond, making it a superb spot for a leisurely afternoon.A must-see in Winterset is the birthplace of the famous director John Wayne, where fans can learn about his early life and career. Additionally, the nearby Covered Bridges of Madison County, including the iconic Roseman Bridge, provide a charming glimpse into the region's heritage and are a popular spot for photography.The town also boasts the Winterset Art Centre, showcasing local artists and hosting various exhibitions throughout the year, enriching the cultural experience for visitors.
Are all fees included in the Winterset holiday homes prices shown on Stayz?
Stayz 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.
Are there any Winterset holiday homes with parking?
Stayz offers a wide selection of holiday homes in Winterset with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Winterset holiday homes?
You can find great discounts on holiday homes in Winterset on Stayz, 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.
Can I change or cancel my Winterset holiday home booking on Stayz?
To find Winterset holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winterset?
A long-stay holiday home in Winterset is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Winterset holiday home?
Book your Winterset holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winterset?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winterset to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.