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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, (66)
"This was great for our extended family to stay. Plenty of room for everyone. "
The price is NZ$1,124
includes taxes & fees
12 Oct - 13 Oct
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

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 NZ$622
includes taxes & fees
6 Oct - 7 Oct
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

Beautiful home minutes from downtown!

9.4 out of 10, Exceptional, (20)
"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 NZ$471
includes taxes & fees
6 Oct - 7 Oct
Beautiful home minutes from downtown!

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 NZ$1,235
includes taxes & fees
6 Oct - 7 Oct
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!

NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!

9.4 out of 10, Exceptional, (70)
"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 NZ$890
includes taxes & fees
5 Oct - 6 Oct
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOL. WE HAVE IT ALL!

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

House of Funk - A Cozy & Eclectic Retreat in Des Moines’s Drake Neighborhood

9.8 out of 10, Exceptional, (13)
"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

Velvet Noir - Sultry City Luxe

10.0 out of 10, Exceptional, (2)
"Clean and well-furnished home with comfortable beds. Great location near downtown and steps away from fun bars and good restaurants. Property managers were available and attentive to our needs."
The price is NZ$590
includes taxes & fees
6 Oct - 7 Oct
Velvet Noir - Sultry City Luxe

Charming 3-bedroom house with WiFi and fitness room and hot tub, playground

2.0 star property
8.6 out of 10, Excellent, (29)
"Stayed here with a handful of my buddies for the weekend of a wedding and the space was perfect! Being so close to the airport definitely saved us a ton of trouble. Plenty of room to hang out with more friends who were in town and the host was very accommodating of that!!"
The price is NZ$490
includes taxes & fees
5 Oct - 6 Oct
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground

Recently Remodeled! Charming 2-bedroom bungalow in terrific DSM neighborhood

9.6 out of 10, Exceptional, (9)
"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 NZ$1,243
includes taxes & fees
8 Oct - 9 Oct
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!

Marisol's Cozy House

9.2 out of 10, Wonderful, (5)
"Family of 6 stayed for 2 nights. Comfortable enough for 2 nights. 4 of us for another 2 nights was much better. 6 is tight. 4 is fairly comfy. Cute place. "
The price is NZ$488
includes taxes & fees
6 Oct - 7 Oct
Marisol's Cozy House

NEW! The Palms Mirage House

10.0 out of 10, Exceptional, (2)
"Perfect location and property for girlfriends to gather and stay for high school reunion. Everything we needed to reconnect and enjoy each others company. "
NEW! The Palms Mirage House

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 NZ$305
includes taxes & fees
5 Oct - 6 Oct
Comfortable stay downtown near sculpture park-7

Lovely 2-bedroom apartment in Sherman Hill-4

8.4 out of 10, Very good, (17)
"This was a great location it was about a mile walk to downtown. Very accommodating and excellent communication with host! "
The price is NZ$323
includes taxes & fees
5 Oct - 6 Oct
Lovely 2-bedroom apartment in Sherman Hill-4

Waterbury Treasure!

9.8 out of 10, Exceptional, (10)
"Great home we booked during our time in Iowa for hinterland. It was a great place to escape to after the music festival!"
Waterbury Treasure!

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

The Love Shack: Spacious Family Getaway, 5 bed/3 bath, 10 Minutes from Downtown

2.0 star property
10.0 out of 10, Exceptional, (7)
"Great house for our family to stay and gather between weddings events! Easy to get to and had lots of space to hang out. "
The price is NZ$736
includes taxes & fees
6 Oct - 7 Oct
The Love Shack: Spacious Family Getaway, 5 bed/3 bath, 10 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 NZ$1,427
includes taxes & fees
5 Oct - 6 Oct
Beautiful remodeled historic Drake Univ home minutes from downtown and all metro

Sleepover: Airy 1BD/1BA - Downtown Des Moines

7.6 out of 10, Good, (4)
"A great neighborhood and a great room. Super clean with a really easy check in. Would recommend and would stay again in the future."
Sleepover: Airy 1BD/1BA - Downtown Des Moines
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

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 favorite 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 depends 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 NZ$305 per night. Entering your travel dates in the search wizard you might find 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, Madison County Courthouse and Cedar 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.