Vacation rentals in Winterset

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Top-rated vacation rentals in Winterset

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

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Guest favorite
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 favorite
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 favorite
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, 105 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 favorite
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.

Top guest favorite
Barn in Highland Park
4.98 out of 5 average rating, 297 reviews

“The Miles Barn” Gorgeous Industrial Loft

Welcome to our beautiful open concept industrial loft. Upon entering our cozy abode, you'll find a clean, bright, well decorated home with many great amenities where you can kick back, relax and enjoy your stay. If high ceilings and beautiful polished concrete floors are your thing, you will be in heaven. Steel railings give it a true industrial feel. Everything needed for your stay is well thought out and ready to be used. We hope you love our loft as much as we do! ***Pet Fee is $125***

Top guest favorite
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.
Apartment 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 favorite
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 favorite
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.
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

Top guest favorite
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 favorite
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 favorite
The exterior of a galaxy bell tent is softly illuminated by string lights, highlighting its unique shape. The surrounding area features a natural landscape, with trees visible in the background, creating a serene nighttime setting.
Tent in Perry
4.94 out of 5 average rating, 218 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 favorite
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.
Apartment in Stuart
4.99 out of 5 average rating, 142 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 vacation rentals

When is the best time to visit Winterset?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ331ﺩ.ﺇ419ﺩ.ﺇ444ﺩ.ﺇ389ﺩ.ﺇ466ﺩ.ﺇ477ﺩ.ﺇ474ﺩ.ﺇ459ﺩ.ﺇ466ﺩ.ﺇ455ﺩ.ﺇ444ﺩ.ﺇ415
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Frequently Asked Questions

  • Do house rentals in Winterset have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Winterset. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winterset have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Winterset. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Winterset?

    Yes! Work meets play with ease at over 10 vacation rentals in Winterset featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Winterset?

    Experience the best of Winterset with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Winterset have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Winterset. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winterset have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Winterset. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Winterset?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in Winterset?

    Winterset has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about vacation rentals in Winterset

  • Total vacation rentals

    Explore 10 vacation rentals in Winterset

  • Nightly prices starting at

    Winterset vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

  • Verified guest reviews

    Over 2,000 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Winterset vacation rentals include wi-fi 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