Vacation rentals in Winterset

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winterset

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

%{current} / %{total}1 / 1
Top guest favorite
A vibrant living room features a curvy orange couch, complementing a playful area rug with geometric patterns. A glass window allows natural light to illuminate the space, highlighting the eclectic decor on a nearby shelf. Seating includes a striped chair and a coffee table.
Home in Beaverdale
4.96 out of 5 average rating, 237 reviews

MidCentury, technicolor Ranch w/yard, w+d, parking

- Ranch home in Des Moines' friendly Beaverdale neighborhood - Steps from grocery store, ice cream shop+dining - Blocks to more dining+shops - Less than 5 minutes from Drake University - Around 10 minutes from downtown, Des Moines, Arts Center, parks - Easy access within 15 minutes to suburbs - 1000+ feet with open living, dining and kitchen, 2 beds, 1 bath, laundry and on-site parking - Outdoor front porch, back patio+fire pit - Perfect for a family or two couples ***Send your special requests!

Top 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, 108 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 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
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.

Top guest favorite
A private bedroom features a spacious bed adorned with decorative pillows and a patterned comforter. Two bedside lamps stand on wooden nightstands, alongside a dresser with framed pictures. Natural light filters through a window, brightening the warm-toned wooden flooring.
Guest suite in Ankeny
4.9 out of 5 average rating, 244 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 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
4.88 out of 5 average rating, 208 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, 217 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!

Top guest favorite
A living area is displayed featuring a comfortable dark sofa and a wooden coffee table on a textured area rug. A dining space with four chairs is adjacent to a well-equipped kitchen, visible in the background. Natural light enters through a window dressed with light curtains.
Guest suite in Winterset
4.87 out of 5 average rating, 127 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.

Popular amenities for Winterset vacation rentals

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 G$2,089 GYD 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