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Check prices for these dates

In two weeks
26 Sept - 28 Sept
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec
In four months
2 Jan - 4 Jan

Featured Cottages in Winterset

Family-friendly Des Moines Retreat w/ Patio!
House (3 Bedrooms) | Interior

Family-friendly Des Moines Retreat w/ Patio!

3.0 star property
10.0 out of 10, Exceptional, (1)
Family-friendly Des Moines Retreat w/ Patio!
Charming Winterset Vacation Rental w/ Yard & Patio
House (4 Bedrooms) | Interior

Charming Winterset Vacation Rental w/ Yard & Patio

3.0 star property
10.0 out of 10, Exceptional, (1)
"We stayed here on a trip for the Knoxville Nationals. Went to the John Wayne Museum, seen the bridges. The house is a nice house, met many locals at the pharmacy-resturaunt in the square downtown, very friendly, ate at several other local spots, all good service and food. The area is quiet and the house in great shape, clean, had plenty of towels and comfortable beds. Would definitely recommend if you need a place in this area. "
Charming Winterset Vacation Rental w/ Yard & Patio
Secluded St Charles Cabin w/ Gas Grill + Fire Pit!
Interior

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

2.0 star property
Secluded St Charles Cabin w/ Gas Grill + Fire Pit!
Pet-friendly Des Moines Home w/ Fenced Yard!
Outdoor dining

Pet-friendly Des Moines Home w/ Fenced Yard!

3.0 star property
Pet-friendly Des Moines Home w/ Fenced Yard!
Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!
Exterior

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

3.0 star property
Pet-friendly Urbandale Home ~ 8 Mi to Des Moines!
1 Mi to Valley Junction: Pet-friendly Iowa Home
Exterior

1 Mi to Valley Junction: Pet-friendly Iowa Home

3.0 star property
1 Mi to Valley Junction: Pet-friendly Iowa Home
Raccoon River Retreat: Indoor Pool & Outdoor Fun!
House (4 Bedrooms) | Interior

Raccoon River Retreat: Indoor Pool & Outdoor Fun!

3.0 star property
Raccoon River Retreat: Indoor Pool & Outdoor Fun!
'the Lodge' Spacious Afton Cabin Near Fishing!
House (4 Bedrooms) | Front of property

'the Lodge' Spacious Afton Cabin Near Fishing!

2.0 star property
'the Lodge' Spacious Afton Cabin Near Fishing!
1 Mi to Golf: Quiet Waukee Home w/ Fireplace!
House (3 Bedrooms) | Interior

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

3.0 star property
1 Mi to Golf: Quiet Waukee Home w/ Fireplace!
'the Barn' Secluded Home 7 Mi to Afton Lake!
House (6 Bedrooms) | Interior

'the Barn' Secluded Home 7 Mi to Afton Lake!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Plenty of space very secluded and accommodating for everything we needed for a weekend "
'the Barn' Secluded Home 7 Mi to Afton Lake!
15 Mi to Dtwn Des Moines: Pet-friendly Waukee Home
Interior

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

3.0 star property
15 Mi to Dtwn Des Moines: Pet-friendly Waukee Home
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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Top Winterset Hotel Reviews

Find out more about Winterset

Find out more about Winterset

Winterset Cottages information

Number of reviews
Accommodation
12 Cottages
Lowest Price
Highest Price

Frequently asked questions

What is there to do in Winterset near my cottage?
Winterset has enough activities and experiences to keep you on the go for weeks (or months!), beginning with The Winterset Stage. Pammel State Park, Roseman Bridge and Holliwell Bridge are other wonderful attractions. If you have time to spare, Hogback Bridge and John Wayne Birthplace Museum will round off your itinerary nicely.