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Winterset Holiday Rentals

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Holiday Rentals in Winterset

LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
9.8 out of 10, Exceptional, (67)
"This was great for our extended family to stay. Plenty of room for everyone. "
The price is AU$1,023
includes taxes & fees
16 Oct - 17 Oct
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
9.4 out of 10, Exceptional, (57)
"Excellent location and clean property. Plenty of things to do in the area as well as comfortable living space at the property."
The price is AU$989
includes taxes & fees
3 Nov - 4 Nov
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground
2.0 star property
8.4 out of 10, Very good, (30)
"Wonderful property and host! "
The price is AU$451
includes taxes & fees
16 Oct - 17 Oct
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground
Charming Beaverdale 4BR/2BA in central DSM - Safe & Cozy
9.4 out of 10, Exceptional, (26)
"This location had the space, comfort and amenities to make our stay enjoyable. "
Charming Beaverdale 4BR/2BA in central DSM - Safe & Cozy
Luxury condo. 2 car garage, rooftop patio. Perfect for work or play!
10.0 out of 10, Exceptional, (35)
"We loved this place! Fun location"
Luxury condo. 2 car garage, rooftop patio. Perfect for work or play!
Farmhouse Oasis
10.0 out of 10, Exceptional, (15)
"We loved the nearby Amish grocery store."
The price is AU$279
includes taxes & fees
27 Oct - 28 Oct
Farmhouse Oasis
Comfortable stay downtown near sculpture park-7
8.6 out of 10, Excellent, (7)
"We enjoyed our short visit to Des Moines. The space fit our needs nicely. It is an old building with creaky floors, but furnishings are updated. We were close to what we need to do with lots of stores and restaurants near by. "
The price is AU$240
includes taxes & fees
16 Oct - 17 Oct
Comfortable stay downtown near sculpture park-7
House of Funk - A Cozy & Eclectic Retreat in Des Moines’s Drake Neighborhood
9.8 out of 10, Exceptional, (15)
"Great house with plenty of space for hosting a small group get together! The location is close to downtown and easy to get to! "
House of Funk - A Cozy & Eclectic Retreat in Des Moines’s Drake Neighborhood
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
10.0 out of 10, Exceptional, (63)
"This house was perfect for our little girl's weekend getaway! The hot tub was so nice to relax in."
The price is AU$565
includes taxes & fees
10 Nov - 11 Nov
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10
2-bedroom vacation home just 3 minutes drive to Drake University
9.8 out of 10, Exceptional, (46)
"This house was very clean and family friendly. Very easy to locate. I and my family stay over for 3 days . We travel from cleveland to iowa. "
2-bedroom vacation home just 3 minutes drive to Drake University
Beautiful home minutes from downtown!
9.4 out of 10, Exceptional, (21)
"Overall we had a nice time and would come back. It was convenient for visiting family without being in each other’s way."
The price is AU$425
includes taxes & fees
16 Oct - 17 Oct
Beautiful home minutes from downtown!
Beautiful remodeled historic Drake Univ home minutes from downtown and all metro
10.0 out of 10, Exceptional, (53)
"We had 2 families of young adults and teens. Plenty of space for our needs and well located. "
The price is AU$1,291
includes taxes & fees
16 Oct - 17 Oct
Beautiful remodeled historic Drake Univ home minutes from downtown and all metro
Forest Ave Historic Rutledge home 8 beds close to everything in the metro.
9.6 out of 10, Exceptional, (5)
"Very clean and nice place - lots of room and very cozy. Fit all 6 people just fine and was in a good location for things to do. "
The price is AU$596
includes taxes & fees
16 Oct - 17 Oct
Forest Ave Historic Rutledge home 8 beds close to everything in the metro.
Recently Remodeled! Charming 2-bedroom bungalow in terrific DSM neighborhood
9.6 out of 10, Exceptional, (10)
"We stayed for a week and had such a wonderful time. The home is beautiful, clean, comfortable, and the photos are a perfect description. While we were there we saw fireflies, an owl, bunnies, a doe and fawn, chipmunks, squirrels, cardnials, and many others birds. The neighborhood is quiet and beautiful. We absolutely would stay here again."
Recently Remodeled! Charming 2-bedroom bungalow in terrific DSM neighborhood
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!
9.8 out of 10, Exceptional, (64)
"Absolutely wonderful property! We are looking into booking again for next year, there was something for everyone to do! Thank you for sharing this little piece of paradise!"
The price is AU$1,132
includes taxes & fees
16 Oct - 17 Oct
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!
URBAN RETREAT - 4 BEDROOM HOUSE, FAMILY FRIENDLY with ARCADE, GAMES..
2.0 star property
10.0 out of 10, Exceptional, (22)
"Very nice and clean house, was perfect for what we needed!"
URBAN RETREAT - 4 BEDROOM HOUSE, FAMILY FRIENDLY with ARCADE, GAMES..
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!
9.4 out of 10, Exceptional, (71)
"We had a fun time staying at this house. We visited downtown Des Moines and had a great time at Adventureland. The only suggestion would be to have some dish towels in the kitchen. The arcade games, ping pong table and skee-ball were popular with the kids. "
The price is AU$805
includes taxes & fees
16 Oct - 17 Oct
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!
Cozy Waterbury VRBO next to Willow on Grand Events Center and Val Air Ballroom
9.6 out of 10, Exceptional, (24)
"House is mostly updated and huge! We had a good stay. "
Cozy Waterbury VRBO next to Willow on Grand Events Center and Val Air Ballroom
Charming 4 Bedroom Home With Beautiful Backyard
9.4 out of 10, Exceptional, (70)
"The house is clean and nice. Quite little neighborhood far enough out of downtown to be quite but close enough to be very convenient to get to any activity at all the convention centers."
Charming 4 Bedroom Home With Beautiful Backyard
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
8.4 out of 10, Very good, (5)
"Excellent location and apartment. Very private yet close to everything. Highly recommend it."
The price is AU$275
includes taxes & fees
16 Oct - 17 Oct
1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winterset Hotel Reviews

Find out more about Winterset

Everything you need to know about Winterset holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winterset holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winterset holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winterset holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winterset. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winterset holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winterset holiday rentals we have selected for you start as low as AU$240 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winterset rentals

At Expedia, we put the best Winterset holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winterset rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winterset holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winterset. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Winterset?

Yes, there are holiday rentals close to the most popular sights in Winterset, or you can select a more secluded option if you're looking for a relaxing stay. Winterset is known for its shopping and restaurants. Make sure you have time to check out the bars while you're in the area.

What are some of the best holiday rentals that Winterset has to offer?

LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!: This holiday home rental outside of Winterset is located next to a golf course, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Winterset?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Winterset stay.

What can I see and do in Winterset?

Cultural attractions include John Wayne Birthplace Museum and The Winterset Stage, whereas Pammel State Park is one spot to enjoy nature. While here, Cedar Bridge and Roseman Bridge are other places worth a visit.

What are holiday rentals like in Winterset?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winterset. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips or small group gatherings.