Holiday houses in Winterset

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Top-rated holiday rentals in Winterset

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Guest favourite

Home in Winterset

4.98 out of 5 average rating, 103 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

Cottage in Redfield

4.99 out of 5 average rating, 102 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

Top Guest favourite

Tiny home in Norwalk

4.98 out of 5 average rating, 115 reviews

Charming 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

Apartment in Winterset

4.94 out of 5 average rating, 362 reviews

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.

Top Guest favourite

Cabin in Cumming

4.98 out of 5 average rating, 160 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.

Superhost

Apartment in Winterset

4.84 out of 5 average rating, 440 reviews

Iowa Nice Winterset

You are renting a piece of “Iowa Nice”, please read my reviews, the entire Lower level but must pass through my area to go down stairs. I greet every guest so it is IMPORTANT to let me know your arrival time. IowaNice is a real thing not just a saying. I will be happy to cook Iowa home style meals for you, just let me know ahead of time. Also available for child care and dog sitting. Long term guest can have laundry done. I want you to know what small town Iowa is like.

Top Guest favourite

Guest suite in Ankeny

4.9 out of 5 average rating, 242 reviews

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.

Top Guest favourite

Home in Des Moines

4.97 out of 5 average rating, 167 reviews

Woodland Heights hist. district house on the hill.

Beautiful historic duplex house in the heart of woodland heights. Walking distance to downtown and next to Ingersoll avenue which is full of shops, bars, restaurants and more. Our place allows 2 parking spots on site with a side entrance to your upstairs Airbnb. The 800+ sq ft space includes a private kitchen, bathroom, bedroom, living room, and balcony with views of downtown. Picnic table and grassy area below balcony can be used on those nice Iowa days.

Guest favourite

Cottage in Minburn

4.95 out of 5 average rating, 324 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.

Top Guest favourite

Tent in Perry

4.94 out of 5 average rating, 206 reviews

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.

Top Guest favourite

Apartment in Stuart

4.99 out of 5 average rating, 138 reviews

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!

Guest favourite

Guest suite in Winterset

4.87 out of 5 average rating, 126 reviews

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.