Discover Weekends in Winterset, IA

Your perfect weekend getaway awaits just 35 minutes from Des Moines, Iowa. Enjoy everything Winterset and Madison County has to offer!

Loft Apartment - 1 BRHouse - 2 BR

Things to do in Madison County

Living room designed in a Scandinavian style with boho-inspired elements, featuring wicker furniture, wooden flooring, and a neutral color palette.
Spacious Living Areas
Our vacation rentals feature bright and airy living spaces, perfect for relaxing with family or friends after a day of exploring Winterset.
Island, long counter, sink, major appliances, wall clock, pendant lights, and hardwood floor.
Fully Equipped Kitchens
Enjoy the comforts of home with our fully equipped kitchens, ideal for preparing delicious meals or enjoying takeout from local favorites.
Winding path through golden grass at sunset on dunstable downs
Serene Outdoor Spaces
Unwind in our charming outdoor spaces, where you can soak up the natural beauty of Winterset and enjoy a peaceful retreat.
Photo of two boys having fun on a summer vacation in a house with a swimming pool, while their mom is relaxing over the book she is reading in a sun bed
Family-Friendly Amenities
With kid-friendly features and plenty of room to play, our Winterset vacation homes are the perfect choice for your family's getaway.
Group of cheerful young tourists walking through a city street market, smiling and talking as they browse stalls and enjoy a social travel experience.
Proximity to Local Attractions
Stay just minutes away from Winterset's historic attractions and vibrant community spots, making it easy to explore and enjoy.
Modern apartment interior. 3D generated image. All wall artworks are my own images and are just simple 3D generated pictures.
Cozy Bedrooms
Retreat to our comfortable bedrooms, designed for a restful night's sleep, ensuring you wake up refreshed and ready for the day.

What Our Guests Are Saying About Their Winterset Vacation Rentals

We had a fantastic stay at Weekends in Winterset! The home was cozy and beautifully decorated, making it the perfect place to unwind after a day of exploring. We especially loved the outdoor space; sipping coffee on the porch was such a relaxing treat. We'll definitely be back!
E
Emily Johnson
Vacationer
As a family of four, we often struggle to find family-friendly lodging that feels welcoming. Weekends in Winterset exceeded our expectations! The kids loved the spacious yard, and we all enjoyed the nearby attractions. It truly felt like a home away from home!
M
Mark Stevens
Father and Explorer
What a gem! This Winterset vacation home offered everything we needed for a cozy getaway. The hosts were incredibly welcoming, and the local recommendations made our stay special. Don't miss the nearby parks; they're absolutely stunning!
S
Sarah Patel
Travel Blogger
Travel Tales
I was looking for a weekend getaway in Winterset, and Weekends in Winterset was the perfect choice. The amenities were top-notch, and the natural light flooded the space with warmth. It was the relaxing retreat I needed!
J
John Miller
Retired Teacher

Explore Your Perfect Vacation Rental in Winterset, IA

Unwind in our cozy and inviting Winterset vacation homes, designed for families and weekend getaways alike. Experience the warmth of home as you create unforgettable memories surrounded by the natural beauty of Iowa. Discover the charm of Winterset today!
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