Winterset Holiday Rentals

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Holiday Rentals in Winterset

Holiday Home in Woodland Heights

9.4 out of 10, Exceptional, (60)
"Thanks so much! We enjoyed the stay with our family"
United States
Julia C.
The price is NZ$874
includes taxes & fees
23 Nov - 24 Nov
SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!

Holiday Home in West Des Moines

9.8 out of 10, Exceptional, (67)
"Used this place for a rehearsal dinner and getting ready for the wedding and it worked out perfect"
United States
Lane B.
The price is NZ$1,291
includes taxes & fees
1 Dec - 2 Dec
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!

Holiday Home in Waukee

9.8 out of 10, Exceptional, (68)
"There was a lot of room to spread out. Three bathrooms was a big bonus. Had a great space in the living room for our team meeting, and everyone liked hanging out together in the spacious basement. Enjoyed breakfast all together, with plenty of seating. Nice to have Hy-Vee nearby to grab breakfast food."
United States
Chris H.
The price is NZ$978
includes taxes & fees
24 Nov - 25 Nov
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

Holiday Home in Downtown Des Moines

10.0 out of 10, Exceptional, (40)
"A great place to stay if visiting Des Moines!"
United States
Justine
The price is NZ$455
includes taxes & fees
1 Dec - 2 Dec
Downtown Skyline Views in Modern Townhome with Rooftop Patios

Holiday Home in North of Grand

9.4 out of 10, Exceptional, (70)
"We really enjoyed our stay. Check in was easy. "
United States
Jenny W.
Charming 4 Bedroom Home With Beautiful Backyard

Condo in Downtown Des Moines

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."
United States
Nicole P.
The price is NZ$606
includes taxes & fees
23 Nov - 24 Nov
Velvet Noir - Sultry City Luxe - Sleeps 8+

Holiday Home in Des Moines

9.6 out of 10, Exceptional, (25)
"This worked out great for us while we were in town for a wedding. Plenty of room for 4 of us and a dog!"
United States
Mona J.
The price is NZ$489
includes taxes & fees
30 Nov - 1 Dec
Beautiful home minutes from downtown!

Condo in West Des Moines

9.4 out of 10, Exceptional, (3)
"Great host and location of property "
United States
Danielle B.
The price is NZ$585
includes taxes & fees
30 Nov - 1 Dec
Modern Luxury West Des Moines Condo

Holiday Home in Woodland Heights

10.0 out of 10, Exceptional, (66)
"Wonderful, Close to everything we wanted to do. Very clean and had comfy bed "
United States
M&S D.
The price is NZ$587
includes taxes & fees
24 Nov - 25 Nov
The Cow Tipper: Near Everything - SPA - Game Room - Fire Pit & Patio - Sleeps 10

Holiday Home in West Des Moines

9.4 out of 10, Exceptional, (180)
"Lovely place to stay! Well cared for and lots of amenities. Thank you for such a charming place to rest while we were visiting Des Moines!"
United States
Christine H.
The price is NZ$856
includes taxes & fees
25 Nov - 26 Nov
Walnut Place a Charming Home in Historic Valley Junction area of West Des Moines

Holiday Home in Drake

9.8 out of 10, Exceptional, (6)
"Great location. Close to Drake. Clean home. Great space for our trip."
United States
Katie H.
The price is NZ$789
includes taxes & fees
23 Nov - 24 Nov
Spacious 4-bedroom house central to Des Moines near Drake Univ. Fenced yard

Holiday Home in Waveland Park

9.8 out of 10, Exceptional, (49)
"Great place to stay"
United States
Ben C.
2-bedroom vacation home just 3 minutes drive to Drake University

Cottage in Woodland Heights

2.0 star property
Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping

Holiday Home in Drake

9.6 out of 10, Exceptional, (35)
"Nice, clean property with lots of space. Conveniently located, a very short distance from city of Des Moines. Papa John's Pizza and a gas/convenience store is within walking distance. The hot tub was great, well maintained. "
United States
Sheila G.
Hot Tub, Fenced Yard, Games, Office/Gym + Pets Ok!

Holiday Home in Urbandale

9.6 out of 10, Exceptional, (11)
"Clean and well kept, nice place to stay "
United States
Cooper L.
The price is NZ$536
includes taxes & fees
23 Nov - 24 Nov
Newly remodeled 3-bedroom ranch with pool table, patio, and grill in Urbandale.

Holiday Home in Greater South Side

2.0 star property
8.4 out of 10, Very good, (33)
"Nice place for the family! "
United States
Brandon G.
The price is NZ$573
includes taxes & fees
23 Nov - 24 Nov
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground

Holiday Home in Clive

10.0 out of 10, Exceptional, (2)
"Spacious, comfortable and welcoming. Well supplied. "
United States
Patricia D.
The price is NZ$1,010
includes taxes & fees
23 Nov - 24 Nov
Convenient functional quiet 5 bedroom 3 bath home in Clive.

Apartment in Drake

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. "
United States
Sydney O.
The price is NZ$679
includes taxes & fees
23 Nov - 24 Nov
Forest Ave Historic Rutledge home 8 beds close to everything in the metro.

Apartment in Woodland Heights

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."
United States
Tom G.
Sleepover: Airy 1BD/1BA - Downtown Des Moines

Apartment in Downtown Des Moines

8.4 out of 10, Very good, (18)
"Great place for overnight stay! Clean and parking was easy. Upstairs neighbors were a little loud, but other than that it was a great place to stay after our concert."
United States
ADRIENNE C.
The price is NZ$259
includes taxes & fees
23 Nov - 24 Nov
Lovely 2-bedroom apartment in Sherman Hill-4
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 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$259 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?

SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!: This holiday home rental outside of Winterset offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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. Make the most of games in this rental home to help you unwind.

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, Clark Tower 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.