Holiday rentals in Macksburg

Raccoon River Retreats

Come & experience the magic of this unique getaway,where the warmth of a renovated 1900's home meets the natural wonders of the Raccoon River. 30min from DSM,Ia.Whether you enjoy an adventure on the river of kayaking, paddle boarding, fishing,a peaceful moment along the biking trails,cozy up with a cup of coffee by the fireplace or a fire in the outdoor fire pit,our retreat has an idyllic setting to create lasting memories.A scenic landmark, local restaurant,Dairy shop & Dollar General are near

Aerie Loft Apartment with view that sleeps 7

This elevated second story apartment has an incredible view of the historic downtown square and courthouse. Bring your group to be in a centralized location near dining/bars , shopping, museums, and a movie theatre. Accommodations for a group of seven is ideal for getaways or special occasions. The unique relief art sculpture of a tree and eagles will captivate you. A full kitchen with all the essentials. 6 beds and spacious 3/4 bath and a second 3/4 bath opened for 5 or more guests.

Luxury Studio- 1 Block to Town Square

Step into our luxurious studio that seamlessly blends style and functionality. This elegant space greets you with the warm glow of a modern fireplace, perfect for cozy evenings after a day of exploration in the quaint town square located just a block away. The studio's clever design boasts a well-equipped workstation, the sleek and space-saving Murphy bed transforms the room from a productive workspace by day to a tranquil sleeping area by night. The promise of an exquisite stay awaits you.

Farmhouse 1910

The whole group will enjoy easy access to everything from this centrally located home. With 4 bedrooms and 3 baths, this gorgeous, all-electric home has it all. Sleeping 10 comfortably, we boast NO STAIRS (!). The converted garage makes an incredible crafting/quilting spot for you and your friends! *NOTE - rates are based on a per person fee with a base rate of $150 per night (or three guests). Close to Creston, Afton and the lakes, we have ample parking for vehicles, boats or trailers.

2‑BR Apt. Near Uptown w/ Wi-Fi

Welcome to our cozy 2-bedroom apartment in a historic two-story home just steps from Uptown Creston. Walk to local restaurants, shops, and bars while enjoying a space that blends original charm with modern updates. The apartment is located on the 2nd floor and offers off-street parking. Sleeping arrangements: • Bedroom 1 – Queen bed • Bedroom 2 – Queen bed • Large couch suitable for an additional guest if needed Please note this is a compact apartment designed for relaxing and sleeping.

The Legacy Stone House

The most unique stay in Winterset! Legacy Stone House AirBnB is a historic residence located one mile east of Winterset, Iowa. Built in 1856 during the Settlement Era of Madison County, it is one of nearly 100 stone houses built during that time in the area. Officially named the William Anzi Nichols House, it is listed on the National Register of Historic Places. Convenient centralized location if visiting Madison County’s six covered bridges and two minutes from grocery, gas and dining.

Haven Creek Ranch

Escape to this peaceful, charming 100-year-old farmhouse nestled near 1,000+ acres of public hunting land. Enjoy private hiking trails, quiet country nights, and rustic charm in every corner. Perfect for hunters, hikers, families, or anyone craving a break from city life. Unplug, unwind, and reconnect with nature in this serene, secluded retreat. Full of warmth and character—an authentic country escape. The home features 3 bedrooms, 1 bath, and comfortably sleeps up to 8 guests.

The Country Oasis

Welcome to your perfect retreat—where comfort, style, and thoughtful details come together. The Country Oasis offers beautifully designed spaces to relax, recharge, and connect. This inviting vacation rental features 2 bedrooms and 2 bathrooms, making it perfect for your next getaway. With modern amenities and comforts such as a hot tub, fireplace, and various gathering spaces both indoors and out, The Country Oasis guarantees a memorable experience with friends and family.

The Roost at Speckled Hen Farms.

Explore the Iowa countryside with this 70's ranch as your relaxing base camp. Situated on 5 acres of rolling hills in rural Madison County, Iowa, this centrally located homestead has something for every kind of traveler. The charming town of Winterset is just minutes away, as well the historic Covered Bridges, wineries, breweries, parks and more. Located next to Speckled Hen Farms farm store and Lone Oaks Farm, you can take in an occasional music event or class!

Relaxing galaxy bell tent getaway

Come sleep under the stars in this cozy galaxy bell tent. You can enjoy a good nights sleep in the comfortable King bed and stay comfortable with an air conditioner and heater. There is also a fridge for keeping your food fresh. Soak up nature while you hike the trails around Oak Haven Acres, a 32 acre farm in rural Iowa. For your security we have a trail camera at the beginning of the driveway that won’t intrude on your privacy.

House in Creston

Relax with the whole family in this cute cozy house. The house sits on a large corner lot in a quiet neighborhood. 3 bedrooms, 1 king and 3 single beds. Even a toy room for the little ones. Relax in one of the 4 recliners and watch a movie on the big screen tv. Plenty of room to park the boats, electric for charging available and a fish cleaning table is available. Perfect place for your hunting or fishing trip. Pets welcome

The 1894 by Doe A Deer | 2 br, 1 bath apartment

Welcome to The 1894 by Doe A Deer - a newly renovated 2 bedroom spacious apartment located in historic downtown Stuart! Enjoy restaurants, boutiques and coffee just steps from the front door. Relax and enjoy the view from your new favorite small town spot. Perfect for getting ready with your wedding party, families, girls trips, anniversaries & more! We can’t wait to host you!