
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.

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!

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 Suite Iowa Life
THE BEST VALUE IN WINTERSET Don’t spend your money on an impersonal hotel when you can stay at our “home away from home!”! This Suite is located on the main level of our home where we live and work. It is a PRIVATE, FULLY EQUIPPED APARTMENT, UNSHARED SPACE. Separate entrance. Pets allowed. Access to yard and beautiful country views. * NEW MATTRESS * November 2023 Large backyard, grill, fire pit, close to town & centrally located amongst the six bridges. PLEASE READ FULL DESCRIPTION.

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

Spacious One Bedroom apartment
This apartment features over 1,200 square feet of living space. Enjoy a full kitchen with granite countertops, full oven, full refrigerator, dishwasher, and microwave oven. Spend time playing ping pong with family or enjoy popcorn and a movie. The location is situated in a quiet and safe neighborhood about 20 minutes from downtown Des Moines. Weather your planning a get-away with family or friends or a relaxing time alone we want our home to be your oasis.

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

Etta’s Place - private 1b/1b - MidCentury Modern
We love our neighborhood and are excited to share it with you! We have partnered with local restaurants, bars, coffee shops, boutiques, & tea shops to offer exclusive discounts to guests of “Etta’s Place.” It’s our hope that this Airbnb allows you to enjoy the wonderful Ingersoll District. Des Moines is a great place to visit, lots of outdoor activities, amazing food, and unique experiences around every corner!

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!

2 BR fully furnished private condo sleeps 4
2 blocks from courthouse square businesses. High speed internet 250 meg. 2 private parking lots. 30 min from Des Moines. Walking distance to the corner tavern. Gas station across the street. Please note, address is 314. AirBnB doesn't recognize the address and it defaults to 316. Private residence is 314 door in front of the driveway on the North side of the house.
Popular amenities for Winterset holiday rentals
Other great holiday rentals in Winterset

New Arrival Peaceful Comfort Calm & Private

Country peace

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

Iowa Nice Winterset

Charlie's Place

The Victoria is work friendly, fenced, patio/grill

Squareview Stays - Modern Apartment on The Square

Rittenhouse Inn
When is the best time to visit Winterset?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £68 | £86 | £91 | £80 | £95 | £98 | £97 | £94 | £95 | £93 | £91 | £85 |
| 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 £8 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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