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

Check dates for Winterset hotels

Cottages in Winterset

Cozy Cottage Near Downtown Walkable to Dining and Boutique Shopping

Des Moines IA

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

Washer

Dryer

Family-friendly Des Moines Retreat w/ Patio!

Des Moines IA

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

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.

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

Saint Charles IA

When you stay at this cottage in Saint Charles, you'll be 10 minutes by car from Imes Bridge.

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.

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

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 Casey's Center and Jordan Creek Town Center.

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 Casey's Center and Southridge Mall.

Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!

Urbandale IA

Located in Urbandale, this cottage is within a 15-minute drive of Casey's Center and Jordan Creek Town Center.

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.

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.