Osceola County Vacations & Trips from $439
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Your Osceola County Vacation
With an Osceola County vacation package, you can forget about the hassle of planning and simply focus on experiencing what this interesting destination has to offer. Can't decide what should come first? Sibley is one of the most popular cities to explore during your trip to Osceola County. Expedia is a one-stop shop when it comes to organizing your Osceola County vacation. From accommodations and flights, to activities and rental cars, we're here to help you create a travel experience like no other.
Top destinations in Osceola County
Sibley
The Latest Osceola County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Valley Inn
University Heights
$439
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Sioux Falls (FSD)
7.8/10 Good! (1,010 reviews)
For someone with mobility issues, an excellent room. Room was very close to entrance, located on 1st floor, right across hall from elevator, a recliner , and bathroom had nice walk in shower with a seat and many grab bars. Could not have asked for anything nicer.
Reviewed on Sep 1, 2026
Hotel On Phillips
Downtown Sioux Falls
$608
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Sioux Falls (FSD)
9.6/10 Exceptional! (1,565 reviews)
I travel the country and this is one of the best hotels I have stayed at. I put it up there with the W, Ritz, and Fairmont.
Reviewed on Sep 3, 2026
Find the Best Osceola County Vacation Packages
Osceola County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Eppley Field Airport (OMA) |
Osceola County Hotel Deals
Sibley Inn
1108 2nd Avenue Sibley IA
Fully refundableReserve now, pay when you stay
$72 nightly
$79 total
Oct 4 - Oct 5
Total with taxes and fees
Lake Okoboji Resort & Conference Center
1405 Highway 71 Okoboji IA
Fully refundableReserve now, pay when you stay
$96 nightly
$106 total
Sep 6 - Sep 7
Total with taxes and fees
Vintage Block Inn & Suites
1107 Sanborn Ave Okoboji IA
$90 nightly
$98 total
Oct 4 - Oct 5
Total with taxes and fees
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.
Stay near popular Osceola County attractions
Sibley Golf And Country Club
8.0/10 (3 reviews)
Enjoy a round of golf in Sibley at Sibley Golf And Country Club. Discover the area's entertainment venues and churches.
Albert W. McCallum Museum
8.0/10 (3 reviews)
You can spend an afternoon browsing the exhibits at Albert W. McCallum Museum during your travels in Sibley. Discover the area's entertainment venues and churches.
Sibley Central Park
8.6/10 (14 reviews)
Explore the great outdoors at Sibley Central Park, a lovely green space in Sibley. Discover the area's entertainment venues and churches.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
