Winterset Vacation Rentals

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Vacation Rentals in Winterset

SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!

Des Moines IA

$455 nightly

$510 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

With a stay at this vacation home in Des Moines (Woodland Heights), you'll be within a 15-minute drive of Casey's Center and Iowa State Fairgrounds.

Pool

Kitchen

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

West Des Moines IA

$676 nightly

$757 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

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 Casey's Center.

Hot Tub

Kitchen

Downtown Skyline Views in Modern Townhome with Rooftop Patios

Des Moines IA

$211 nightly

$236 total

Dec 7 - Dec 8

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Des Moines, a 3-minute drive from Casey's Center and 10 minutes from Iowa State Fairgrounds.

Kitchen

Washer

Spacious 4BR Home • WiFi • Family-Friendly • Waukee

Waukee IA

$337 nightly

$377 total

Jan 2 - Jan 3, 2026

Total with taxes and fees

With a stay at this vacation home in Waukee, you'll be within a 10-minute drive of Jordan Creek Town Center and Windfield Park.

Kitchen

Washer

Charming 4 Bedroom Home With Beautiful Backyard

Des Moines IA

With a stay at this vacation home in Des Moines (North of Grand), you'll be within a 15-minute drive of Casey's Center and Jordan Creek Town Center.

Kitchen

Pet friendly

Hot Tub, Fenced Yard, Games, Office/Gym + Pets Ok!

Des Moines IA

With a stay at this vacation home in Des Moines (Drake), you'll be within a 15-minute drive of Casey's Center and Jordan Creek Town Center.

Hot Tub

Kitchen

Newly Remodeled Brick Home with wall Sculptures by the Airport

Des Moines IA

$196 nightly

$220 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

With a stay at this vacation home in Des Moines (Southwestern Hills), you'll be within a 15-minute drive of Casey's Center and Iowa State Fairgrounds.

Kitchen

Washer

The Little Brick House - Walkable to the Square Dining & Shopping

Winterset IA

With a stay at this vacation home in Winterset, you'll be within a 10-minute walk of Madison County Courthouse and John Wayne Birthplace Museum.

Washer

Dryer

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

Waukee IA

$439 nightly

$492 total

Dec 7 - Dec 8

Total with taxes and fees

With a stay at this vacation home in Waukee, you'll be next to a golf course, within a 10-minute drive of Jordan Creek Town Center and Hawthorne Plaza.

Hot Tub

Kitchen

Cozy 3-bedroom Beaverdale Brick

Des Moines IA

With a stay at this vacation home in Des Moines (Beaverdale), you'll be within a 15-minute drive of Casey's Center and Jordan Creek Town Center.

Kitchen

Washer

Beautiful home minutes from downtown!

Des Moines IA

$245 nightly

$274 total

Dec 7 - Dec 8

Total with taxes and fees

Located in Des Moines, this vacation home is within a 15-minute drive of Casey's Center and Iowa State Fairgrounds.

Washer

Pet friendly

2-bedroom vacation home just 3 minutes drive to Drake University

Des Moines IA

With a stay at this vacation home in Des Moines (Waveland Park), you'll be within a 15-minute drive of Casey's Center and Jordan Creek Town Center.

Kitchen

Washer

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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.