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Cottages in Osceola

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

≋ The Cottage at Sun Valley Lake ≋

10.0 out of 10, Exceptional, (73)
"This is maybe our 4th or 5th stay--the lake cottage is always clean, well-equipped, and a perfect haven!"
≋ The Cottage at Sun Valley Lake ≋

blue sky cottage!!!!

10.0 out of 10, Exceptional, (3)
"As promoted, Blue Sky Cottage is a mid-1900s gas station renovated into a studio cottage. And what a delightful adaptation of the property - clean, cozy (perfect size for a couple), bright (lots of light in and reflected), well-furnished and stocked, and even a small patio for enjoying the outdoors. Also a great location for our forays to Pawnee Prairie and Dunn Ranch Prairie in search of birds (bobolinks quite prevalent in June). We enjoyed trying to figure out which parts of the building were...
blue sky cottage!!!!

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

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

'the Lodge' Spacious Afton Cabin Near Fishing!

2.0 star property
'the Lodge' Spacious Afton Cabin Near Fishing!

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

2.0 star property
'the Barn' Secluded Home 7 Mi to Afton Lake!

Charming Iowa Home: 1 Mi to Golf

3.0 star property
Charming Iowa Home: 1 Mi to Golf
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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Frequently asked questions

Why book your cottage in Osceola with Expedia?
Expedia has some superb cottages in Osceola, so start planning for an unforgettable stay on nature's doorstep. If you're on a budget, choose how much you want to spend and your preferred property star rating. Or, make use of our filters to search for cottages with a pool or free WiFi. We'll help you find a suitable place whatever your trip looks like.
How can I find cheap cottages in Osceola?
Expedia can help you look for cheap cottages in Osceola. To reserve your ideal stay in a few clicks, try out our handy filter tool to tailor your search results by amenities, star rating and budget.
What is there to do in Osceola near my cottage?
The ideal travel accessory is a well-planned itinerary. Osceola Country Club is a wonderful place to start your exploration of Osceola.