Winterset Cottages

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Cottages in Winterset

Raccoon River Retreat: Indoor Pool & Outdoor Fun!

Adel IA

With a stay at this cottage in Adel, you'll be within a 10-minute drive of Penoach Winery and Island Park.

Pool

Kitchen

Family-friendly Des Moines Retreat w/ Patio!

Des Moines IA

With a stay at this cottage in Des Moines (Drake), you'll be a 1-minute drive from Drake University and 5 minutes from Casey's Center.

Kitchen

Washer

Charming Winterset Vacation Rental w/ Yard & Patio

Winterset IA

With a stay at this cottage in Winterset, you'll be a 4-minute walk from Madison County Courthouse and 7 minutes by foot from John Wayne Birthplace Museum.

Kitchen

Washer

1 Mi to Golf: Quiet Waukee Home w/ Fireplace!

Waukee IA

With a stay at this cottage in Waukee, you'll be within a 15-minute drive of Jordan Creek Town Center and The Triangle.

Kitchen

Pet friendly

Secluded St Charles Cabin w/ Gas Grill + Fire Pit!

Saint Charles IA

When you stay at this cottage in Saint Charles, you'll be 11 minutes by car from Imes Bridge.

Kitchen

Parking included

Home w/ Spacious Yard, 3 Mi to Dtwn Des Moines!

Des Moines IA

With a stay at this cottage in Des Moines (Indianola Hills), you'll be a 5-minute drive from Principal Park and 6 minutes from Casey's Center.

Kitchen

Pet friendly

Endless Fun! Family Home w/ Spacious Yard in Clive

Clive IA

With a stay at this cottage in Clive, you'll be within a 15-minute drive of Jordan Creek Town Center and Drake University.

Kitchen

Dryer

Pet-friendly Des Moines Home w/ Fenced Yard!

5901 SE 25th St Des Moines IA

With a stay at this cottage in Des Moines, you'll be within a 15-minute drive of Principal Park and Casey's Center.

Kitchen

Washer

Pet-friendly Home 2 Mi to Downtown Des Moines!

Des Moines IA

With a stay at this cottage in Des Moines (Columbus Park), you'll be within a 5-minute drive of Principal Park and Casey's Center.

Kitchen

Pet friendly

15 Mi to Dtwn Des Moines: Pet-friendly Waukee Home

Waukee IA

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

Kitchen

Washer

1 Mi to Valley Junction: Pet-friendly Iowa Home

West Des Moines IA

With a stay at this cottage in West Des Moines, you'll be within a 10-minute drive of Drake University and Casey's Center.

Kitchen

Pet friendly

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.