Holiday houses 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
4.9 out of 5 average rating, 139 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
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, 119 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
The exterior of the house is visible, featuring light-colored siding and traditional shutters on the windows. A charming old wagon wheel is positioned in the foreground, alongside a leafy tree. The inviting front steps lead to the entrance of the home.
Home in Indianola
4.99 out of 5 average rating, 194 reviews

The Hen House

The wonderfully remodeled home based on 55 acres overlooking mature trees and a large pond. The house has 3 bedrooms and 1 1/2 baths. Laundry is available to use as well. Kitchen is fully stocked for your cooking enjoyment and a gas grill is offered as well to use. This house is perfect for families, small groups, or business trips. Situated just 20 minutes from Des Moines airport, and 25 minutes from downtown Des Moines, you will be able to experience the quiet and beautiful scenery to enjoy.

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, 105 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
4.99 out of 5 average rating, 137 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
A comfortable living area features a large smart television on a wooden console, complemented by a stylish area rug. Indoor plants are positioned near the sliding glass doors, which provide natural light and a view of the outdoor deck. A decorative lamp and wall clock enhance the space.
Guest suite in Waukee
4.99 out of 5 average rating, 332 reviews

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.

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.
Apartment in Winterset
4.94 out of 5 average rating, 374 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, 168 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
The two-story farmhouse features a white exterior and a welcoming front porch, adorned with potted plants. A staircase leads to the entrance, flanked by a neat lawn. An American flag is displayed, adding to the home's charm and character.
Home in Earlham
4.97 out of 5 average rating, 116 reviews

Friendly Quarters

This charming location is a farmhouse style home built in 1914. Easily found on the main street through town, a one block walk in any given direction will put you at the center of the city. A grocery story, eating establishments, gift shops and community center are conveniently located in the downtown area. Friendly Quarters operates as a non-profit organization to support the missions and ministries of Earlham Friends (Quaker) Church located right next door.

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
4.96 out of 5 average rating, 349 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
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
4.95 out of 5 average rating, 224 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
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, 156 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$154 NZD$195 NZD$207 NZD$181 NZD$217 NZD$222 NZD$222 NZD$227 NZD$217 NZD$224 NZD$222 NZD$212 NZD
Avg. temp-5°C-3°C4°C11°C17°C22°C24°C23°C19°C12°C4°C-2°C

Frequently Asked Questions

  • Are there family-friendly house rentals in Winterset?

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

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

    Experience the best of Winterset with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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 air conditioning, over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Winterset

  • Total holiday rentals

    Explore 20 holiday rentals in Winterset

  • Nightly prices starting at

    Winterset holiday rentals start at $85 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,100 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Winterset holiday 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!

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  5. Winterset