
Holiday rentals in Winterset
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Top-rated holiday rentals in Winterset
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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!

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

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.

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.

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.

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.

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.

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

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!

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.

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
Other great holiday rentals in Winterset

Country peace

Kirkwood Manor Condo

Seely Creek Cabin Getaway and Hunting Lodge

Cozy Country Container Stay w/ Hot Tub & Fire Pit!

Iowa Nice Winterset

The Draper-MCM Spacious Ranch minutes to it all

Charlie's Place

Squareview Stays - Modern Apartment on The Square
When is the best time to visit Winterset?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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°C | 4°C | 11°C | 17°C | 22°C | 24°C | 23°C | 19°C | 12°C | 4°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!
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