Holiday rentals in Winterset

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winterset

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Guest favourite
A large Victorian home features a unique turret and a wraparound porch with decorative columns. The well-maintained landscaping includes green grass and trees that provide shade, enhancing the home’s inviting exterior.
Home in Dexter
4.89 out of 5 average rating, 133 reviews

The Victoria is work friendly, fenced, patio/grill

My place is located just off I-80 about 20 min from Jordan Creek town Center...It is work friendly. Workers are welcome! Children are welcome! It has a fenced yard, patio and grill. And the town of Dexter, Iowa has a park within walking distance, a public lake, The Rusty Duck Restaurant, Drew's Chocolates..You'll love my place because of staying in a roomy, unique Victorian home furnished with everything you’ll need! The backyard is now fully fenced providing privacy for your outdoor activities.

Guest favourite
The exterior of Rosehaven is showcased, featuring a charming red facade with white trim. A welcoming porch is adorned with greenery and flowers, framed by well-maintained shrubs and trees. A white picket fence outlines the property, emphasizing its inviting presence in the neighborhood.
Home in Winterset
4.98 out of 5 average rating, 109 reviews

Rosehaven

Enjoy the nostalgic small town charm of Winterset, Iowa while staying at Rosehaven, within walking distance to the town square. Between the historic Madison County covered bridges in the area, the John Wayne museum and his preserved birthplace, as well as the numerous wineries and local events - Winterset is full of reasons to visit and stay at Rosehaven - a short 30 min. drive to Des Moines. Rosehaven is easy to find, with plenty of room for up to 5 or 6 guests. We look forward to having you!

Guest favourite
A high wooden ceiling features exposed beams, creating a rustic atmosphere. A railing offers a view down to a living area with a neutral color palette, where a fireplace and decorative elements can be seen in the background.
Cottage in Redfield
4.99 out of 5 average rating, 106 reviews

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

Guest favourite
A spacious living area features large windows, offering expansive views of the skyline. Modern furnishings include a cozy couch, two accent chairs, and a coffee table. A sleek electric fireplace is positioned beneath a wall-mounted TV, enhancing the contemporary design of the space.
Townhouse in Des Moines
4.93 out of 5 average rating, 121 reviews

This is the best Des Moines has to offer!

Welcome to a beautiful 3 story townhome in the heart of Des Moines. If an upscale modern home with an incredible view is your thing, you will be in heaven. Inside you’ll find a clean, bright and well decorated home with all the amenities you'll need to kick back, relax and enjoy your stay. Minutes from shopping, dining and nightlife. The bike trail is across the street where you can ride to Gray’s Lake or stroll to downtown DSM and enjoy the Farmer's Market, Civic Center and Principal Park.

Top guest favourite
A tranquil scene along a serene pond features a wooden dock with views of mist rising from the water. A cozy mug and an open notebook rest on a wooden surface nearby, inviting relaxation and reflection in a picturesque natural setting.
Tiny home in Norwalk
4.98 out of 5 average rating, 125 reviews

Private *Fall Oasis* Waterfront Tiny House & Sauna

The true definition of rest & relaxation, this unique tiny house is situated on a three-acre pond suitable for catch and release fishing, kayaking, or stand up paddle boarding. Bring your gear and leave your worries behind. Built with special touches and details including stained glass windows and intricate woodwork, this tiny home boasts warmth throughout. Wake up to bird songs and coffee with the sunrise. After a day of fun, take a soak in the wood-burning sauna and relax by the campfire.

Top guest favourite
A comfortable living area features a large smart television on a wooden console, complemented by a stylish area rug. Indoor plants are positioned near the sliding glass doors, which provide natural light and a view of the outdoor deck. A decorative lamp and wall clock enhance the space.
Guest suite in Waukee
4.99 out of 5 average rating, 319 reviews

Waukee 2 Bedroom Private Sweet Suite.

Welcome to our comfortable, newly renovated, private guest suite. This quiet Waukee neighborhood living space includes two bedrooms, one full bath, kitchenette, laundry room, dining space and cozy living room area. Off street parking for one vehicle is available. A private entrance is available from the back deck. Your home away from home features a comfortable king size bed and a full size bed. A smart television is available in the living room and an HDTV is available in one bedroom.

Top guest favourite
The historic stone house is illuminated by warm exterior lighting, showcasing its textured stone wall and charming architectural features. Surrounding lights provide a soft glow in the evening, while trees and foliage can be seen in the background, creating a serene outdoor atmosphere.
Home in Winterset
4.96 out of 5 average rating, 296 reviews

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.

Top guest favourite
An inviting outdoor deck area features a wooden seating arrangement under a metal roof, adorned with string lights. A spacious couch offers comfort, while a long wooden table complements the rustic charm. Lush greenery and open space are visible in the background.
Cabin in Cumming
4.98 out of 5 average rating, 163 reviews

Iconic Iowa - A 1920 Built Country Cabin

This 1920 Log Cabin sits at the beginning of the Madison County covered bridges Scenic Byway and features 2 rural country acres of space and a wonderfully remodeled home with loads of character and style. Situated just 10 minutes south of the West Glen area of West Des Moines and 25 minutes from downtown Des Moines, you'll experience the quiet and beauty of rural Iowa while being close enough for shopping or to go out for a nice dinner or evening show. This is a great getaway.

Guest favourite
An open living area displays a large smart TV beside a glass coffee table with snacks. A sectional couch with orange accent pillows provides seating, while a stylish accent chair and a mini cocktail bar showcase the inviting space. The kitchen and dining area are visible in the background.
Serviced apartment in West Des Moines
4.97 out of 5 average rating, 120 reviews

Stylish & Spacious| Pool| NintendoSwitch| King bed

Welcome to WDSM! Spacious unit with open floor plan, two private bathrooms, & large private patio overlooking green field. Pool, Free Tanning, Gym. Minutes from Jordan Creek Shopping Center, Top Golf, restaurants, Spare time, Dave & Busters! Walmart, Target, Movie Theatre and more! Detached garage included steps away from secured entrance. Quiet neighborhood, walking/biking trails, & dog park located on site. DT DSM 18 min Airport 18 min East Village 18 min

Guest favourite
A newly remodeled home is showcased, featuring a welcoming facade with a mix of light and dark exterior colors. A concrete driveway leads to the entrance, surrounded by a well-kept lawn and mature trees. A detached garage is visible nearby.
Home in Indianola
4.91 out of 5 average rating, 147 reviews

Charming Home in Indianola

Discover comfort in our newly remodeled 3-bedroom home in the heart of Indianola, Iowa. This charming space boasts modern amenities and stylish decor, providing a cozy retreat for your stay. Enjoy a fully equipped kitchen, spacious living areas, and a modern bathroom. Perfect for families or groups, our home offers a blend of convenience and warmth. Explore nearby attractions or simply relax in our inviting space. Your home away from home awaits in Indianola!

Top guest favourite
A cozy green house with white shutters sits among lush grass and large trees. The front yard includes a small seating area with chairs and a decorative fence, offering a welcoming entryway. The paved walkway leads to the front door, enhancing accessibility.
Cottage in Minburn
4.95 out of 5 average rating, 330 reviews

Kim's Kottage on the RRVT, in Minburn, IA.

This home is perfect for the Cycling Enthusiast, a couple, family or small group of friends. This fully furnished cozy 2 bedroom home is sure to please. Located 1 block from the Raccoon River Valley Bike Trail (75 mile paved loop), 15 minutes from I-80 and 30/40 minutes from the State's Capital City of Des Moines, Minburn is the "Small Town with a Big Heart". There are two City Parks, an outdoor historical roller skating rink & 2 Rest/Bars.

Guest favourite
A wooden deck with a railing features a flower pot and lounge chairs, overlooking a landscaped area with gravel pathways and bushes. The sun sets in the background, casting a warm glow over the open field beyond.
Farm stay in Dallas Center
4.87 out of 5 average rating, 209 reviews

Cozy Farmhouse Apartment near Des Moines

Cozy Farmhouse Apartment perfectly located for easy access to West Des Moines/Waukee/Grimes/Johnston/Adel. Less than a 20 minute drive to an abundance of restaurants, shops, and attractions - not including the great places to eat/visit in town. This spacious 1 bedroom apartment is located on an acreage between Dallas Center and Minburn. Located within 2 miles of Three Sisters Barn, 6 miles of Keller Brick Barn and raccoon River trail

Popular amenities for Winterset holiday rentals

When is the best time to visit Winterset?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$117 SGD$149 SGD$158 SGD$138 SGD$166 SGD$170 SGD$168 SGD$163 SGD$166 SGD$162 SGD$158 SGD$147 SGD
Avg. temp-5°C-3°C4°C11°C17°C22°C24°C23°C19°C12°C4°C-2°C

Quick stats about holiday rentals in Winterset

  • Total holiday rentals

    Explore 10 holiday rentals in Winterset

  • Nightly prices starting at

    Winterset holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,000 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Winterset holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winterset rentals

  • 5 Average rating

    Winterset stays are highly rated by guests – averaging 5 out of 5!

  1. Airbnb
  2. United States
  3. Iowa
  4. Madison County
  5. Winterset