Book Holiday Homes in Winterset

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

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
Stay at this vacation home in Des Moines. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Wells Fargo Arena and Blank Park Zoo are located ...
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
Book a stay at this golf vacation home in Waukee. Enjoy a garden, a pool table, and patios. Popular attractions Jordan Creek Town Center and Hawthorne Center ...
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
Stay at this vacation home in Des Moines. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Wells Fargo Arena and Iowa State Fairgrounds ...
Downtown Skyline Views in Modern Townhome with Rooftop Patios
Save an average of 15% on thousands of hotels when you're signed in
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
The price is NZ$1,704 per night from 9 May to 10 May
NZ$1,704
includes taxes & fees
9 May - 10 May
Book a stay at this family-friendly vacation home in Urbandale. Enjoy free WiFi, a water park, and patios. Popular attractions Wells Fargo Arena and Merle Hay ...
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
Stay at this vacation home in West Des Moines. Enjoy free WiFi, a garden, and patios. Popular attractions Jordan Creek Town Center and Valley Stadium are located ...
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 NZ$1,280 per night from 29 Apr to 30 Apr
NZ$1,280
includes taxes & fees
29 Apr - 30 Apr
Book a stay at this family-friendly vacation home in West Des Moines. Enjoy free WiFi, a garden, and a pool table. Popular attractions Jordan Creek Town Center ...
AMAZING & A PARTY BARN… HOT TUB, PL TBl, PNG PNG, & ARCADE! ACCESS TO POOLS!
Farmhouse Oasis

Farmhouse Oasis

Dallas Center
Stay at this vacation home in Dallas Center. Enjoy a fitness center, patios, and air conditioning. Popular attractions Kinship Brewing Company and Fox Creek ...
Farmhouse Oasis
Charming 3-Bedroom TOWNHOME in WDM

Charming 3-Bedroom TOWNHOME in WDM

2 out of 5
West des moines
Stay at this vacation home in West Des Moines. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Jordan Creek Town Center and ...
Charming 3-Bedroom TOWNHOME in WDM
Spacious Valley Junction Retreat

Spacious Valley Junction Retreat

West Des Moines
Book a stay at this family-friendly vacation home in West Des Moines. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Wells Fargo Arena ...
Spacious Valley Junction Retreat
Don't see what you're looking for?
See all available properties in Winterset
View all properties
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
190 Holiday Homes
Lowest Price
NZ$163
Highest Price
NZ$1,704
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 NZ$163 per night from 26 Apr to 27 Apr
NZ$163
includes taxes & fees
26 Apr - 27 Apr
Stay at this motel in Winterset. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
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 NZ$219 per night from 11 May to 12 May
NZ$219
includes taxes & fees
11 May - 12 May
Book a stay at this business-friendly hotel in Winterset. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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 NZ$203 per night from 27 Apr to 28 Apr
NZ$203
includes taxes & fees
27 Apr - 28 Apr
Book a stay at this business-friendly hotel in Johnston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Stoney Creek Hotel Des Moines - Johnston
Save an average of 15% on thousands of hotels when you're signed in
Hotel Fort Des Moines, Curio Collection by Hilton

Hotel Fort Des Moines, Curio Collection by Hilton

4.5 out of 5
1000 Walnut St, Des Moines, IA
Fully refundableReserve now, pay when you stay
The price is NZ$254 per night from 26 May to 27 May
NZ$254
includes taxes & fees
26 May - 27 May
Stay at this 4.5-star luxury hotel in Des Moines. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean ...
Hotel Fort Des Moines, Curio Collection by Hilton
Don't see what you're looking for?
See all available properties in Winterset
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.