Book Holiday Homes in Winterset

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Featured Holiday Homes in Winterset

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

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

2 out of 5
Des Moines
The price is AU$441 per night from 15 Apr to 16 Apr
AU$441
includes taxes & fees
15 Apr - 16 Apr
With a stay at this vacation home in Des Moines (Greater South Side), you'll be within a 15-minute drive of Wells Fargo Arena and Drake University.
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!

Waukee
The price is AU$924 per night from 16 Apr to 17 Apr
AU$924
includes taxes & fees
16 Apr - 17 Apr
When you stay at this vacation home in Waukee, you'll be next to a golf course, within a 15-minute drive of Jordan Creek Town Center and Drake University.
LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!
Downtown Skyline Views in Modern Townhome with Rooftop Patios

Downtown Skyline Views in Modern Townhome with Rooftop Patios

Des Moines
The price is AU$389 per night from 15 Apr to 16 Apr
AU$389
includes taxes & fees
15 Apr - 16 Apr
With a stay at this vacation home, you'll be centrally located in Des Moines, within a 5-minute drive of Wells Fargo Arena and Drake University.
Downtown Skyline Views in Modern Townhome with Rooftop Patios
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NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!

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

Urbandale
With a stay at this vacation home in Urbandale, you'll be within a 15-minute drive of Drake University and Wells Fargo Arena.
NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!
Comfortable and Spacious 3 Bedroom Home

Comfortable and Spacious 3 Bedroom Home

West Des Moines
With a stay at this vacation home, you'll be centrally located in West Des Moines, a 4-minute drive from Jordan Creek Town Center and 11 minutes from Drake ...
Comfortable and Spacious 3 Bedroom Home
 AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE!  ACCESS TO POOLS!

AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!

West Des Moines
The price is AU$1,217 per night from 16 Apr to 17 Apr
AU$1,217
includes taxes & fees
16 Apr - 17 Apr
With a stay at this vacation home in West Des Moines, you'll be within a 15-minute drive of Jordan Creek Town Center and Drake University.
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!
Farmhouse Oasis

Farmhouse Oasis

Dallas Center
The price is AU$272 per night from 16 Apr to 17 Apr
AU$272
includes taxes & fees
16 Apr - 17 Apr
Located in Dallas Center, this vacation home is within a 15-minute drive of Kinship Brewing Company and The Triangle.
Farmhouse Oasis
Charming 3-Bedroom TOWNHOME in WDM

Charming 3-Bedroom TOWNHOME in WDM

2 out of 5
West des moines
With a stay at this vacation home in West Des Moines, you'll be within a 15-minute drive of Jordan Creek Town Center and Drake University.
Charming 3-Bedroom TOWNHOME in WDM
Spacious Valley Junction Retreat

Spacious Valley Junction Retreat

West Des Moines
With a stay at this vacation home in West Des Moines, you'll be within a 10-minute drive of Drake University and Wells Fargo Arena.
Spacious Valley Junction Retreat
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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.

Winterset Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winterset vacation homes are the perfect way for you to wing it.

Holiday houses in Winterset let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winterset in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winterset adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winterset with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winterset vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winterset Holiday Homes essential information

Accommodation
184 Holiday Homes
Lowest Price
AU$126
Highest Price
AU$1,217
Popular accommodation
Charming 3-bedroom house with WiFi and fitness room and hot tub, playground , LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!, Downtown Skyline Views in Modern Townhome with Rooftop Patios, NEW REMODEL! ARCADE GAMES, PNG PNG, SKEE BALL, ACCESS TO POOLS..WE HAVE IT ALL!, Comfortable and Spacious 3 Bedroom Home, AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!, Farmhouse Oasis, Charming 3-Bedroom TOWNHOME in WDM, Spacious Valley Junction Retreat

Top trending hotels in Winterset

Covered Bridge Inn

Covered Bridge Inn

2.5 out of 5
1312 Cedar Bridge Rd., Winterset, IA
Fully refundableReserve now, pay when you stay
The price is AU$156 per night from 3 Apr to 4 Apr
AU$156
includes taxes & fees
3 Apr - 4 Apr
Located in Winterset, Covered Bridge Inn is within a 5-minute drive of The Winterset Stage and John Wayne Birthplace Museum.
Covered Bridge Inn
Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA

2.5 out of 5
1304 North 4th Avenue, Winterset, IA
Fully refundableReserve now, pay when you stay
The price is AU$245 per night from 16 Apr to 17 Apr
AU$245
includes taxes & fees
16 Apr - 17 Apr
Located in Winterset, Cobblestone Inn & Suites - Winterset, IA is in a rural location, within a 5-minute drive of The Winterset Stage and Madison County ...
Cobblestone Inn & Suites - Winterset, IA
Stoney Creek Hotel Des Moines - Johnston

Stoney Creek Hotel Des Moines - Johnston

2.5 out of 5
5291 Stoney Creek Court, Johnston, IA
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 3 Apr to 4 Apr
AU$193
includes taxes & fees
3 Apr - 4 Apr
Located in Johnston, Stoney Creek Hotel Des Moines - Johnston is in the suburbs, within a 15-minute drive of Jordan Creek Town Center and Drake University.
Stoney Creek Hotel Des Moines - Johnston
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Days Inn & Suites by Wyndham Des Moines Airport

Days Inn & Suites by Wyndham Des Moines Airport

2 out of 5
1901 Hackley Ave, Des Moines, IA
Fully refundableReserve now, pay when you stay
The price is AU$126 per night from 3 Apr to 4 Apr
AU$126
includes taxes & fees
3 Apr - 4 Apr
Located in Des Moines (Greater South Side), Days Inn & Suites by Wyndham Des Moines Airport is within a 10-minute drive of Drake University and Wells Fargo ...
Days Inn & Suites by Wyndham Des Moines Airport
Don't see what you're looking for?
See all available properties in Winterset
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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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^Subject to availability and chosen travel dates.