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.

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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.

Top 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!

Top guest favourite
A spacious kitchen area is paired with a cozy living space. A tree and eagle relief art sculpture adorns the wall, while large windows provide natural light and views of the outdoors. Gray couches face a coffee table, and the kitchen features modern appliances and ample counter space.
Loft in Winterset
5 out of 5 average rating, 98 reviews

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.

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, 124 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.

Guest favourite
Flat in Winterset
4.88 out of 5 average rating, 16 reviews

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.

Top guest favourite
The exterior of a welcoming house is presented, featuring a covered porch with seating. A large front door is visible, along with a second-floor window above the porch. Lush green grass surrounds the home, framed by trees in the background.
Flat in Winterset
4.94 out of 5 average rating, 369 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
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.

Top 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.
Flat 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

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

Top guest favourite
A bright living room features a vivid blue couch and two green accent chairs surrounding a wooden coffee table. Shelves display various decorative items, and a flat-screen television is mounted on the wall. Natural light enters through a window adorned with textured curtains.
Bungalow in Des Moines
4.97 out of 5 average rating, 502 reviews

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!

Top guest favourite
A light-filled kitchen features open shelving adorned with colorful glassware and decorative items. A modern refrigerator and pink microwave complement the white cabinetry. A central island with bar stools offers seating, while a floral arrangement adds a touch of charm.
Flat in Stuart
4.99 out of 5 average rating, 143 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!

Popular amenities for Winterset holiday rentals

When is the best time to visit Winterset?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price₹7,953₹10,074₹10,692₹9,367₹11,222₹11,488₹11,399₹11,046₹11,222₹10,957₹10,692₹9,985
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 ₹884 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