An aerial view of a coastal city with high-rise buildings, a curved waterfront promenade, and a beach.

Osceola County Holidays

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to €900 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Osceola County

The Latest Osceola County Holiday Packages

Price found within the past 48 hours. Click for updated prices.
  • 29 Dec - 3 Jan

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.4/10 - Very good (3,187 reviews)
    "Charged for an extra night that we didn’t stay and called and was told a reimbursement was completed. Five days later, the full charge for the night we didn’t stay posted in my account and with no reimbursement. When I called again, was told there was nothing they could do because the reimbursement was “released” and I would have to wait to talk to a manager when they arrived which would not be until the nighttime hours."
    Reviewed November 14, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,271
    €1,046
    per traveller
    found 7 hours ago
    Hotel Felix River North/Magnificent Mile
  • 29 Dec - 3 Jan

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.6/10 - Excellent (2,414 reviews)
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,472
    €1,113
    per traveller
    found 7 hours ago
    Hotel Saint Clair- Magnificent Mile
  • 29 Dec - 3 Jan

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,585 reviews)
    "LOVE this hotel! Location is perfect and you can walk everywhere! Just wished they had a pool"
    Reviewed November 14, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,507
    €1,213
    per traveller
    found 7 hours ago
    Swissotel - Chicago
  • 29 Dec - 3 Jan

    Sports Illustrated Resorts Chicago + Flight

    Downtown Chicago
    5 nights
    3.5 star property
    9.0/10 - Wonderful (1,541 reviews)
    "Very clean and comfortable. Valet was helpful and kind"
    Reviewed November 13, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,367
    €1,116
    per traveller
    found 7 hours ago
    Sports Illustrated Resorts Chicago
  • 29 Dec - 3 Jan

    InterContinental Chicago Magnificent Mile by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.2/10 - Wonderful (3,429 reviews)
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,399
    €1,159
    per traveller
    found 7 hours ago
    InterContinental Chicago Magnificent Mile by IHG

Discover the most popular places to visit in Osceola County

Osceola County Hotel Deals

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.

Frequently Asked Questions

How much does an Osceola County holiday package cost?

Browse and book everything in one place with our Osceola County holiday packages, which start from only €1,046. Select the flights and hotels that match your travel plans. Then, add on a few tours or experiences for an incredible adventure.

How do I get a cheap travel package to Osceola County?

Booking a hotel and flight together with Expedia won't just save you time — it'll save you a pretty penny too. An Osceola County holiday package makes it a breeze to put together your perfect trip. With more than 550 airlines all over the world to pick from, finding flights that fit your busy schedule won't be an issue. Not only that, we have over 1,000,000 hotels globally to choose from. Now that's choice! Whatever your budget, Expedia brings the world within your reach.

What are the top hotels in Osceola County?

When it comes to properties in Evart, Osceola Grand Hotel and Private Country Abode By Wells Lake Michigan are a couple of favourites. If you're considering heading to Le Roy, Mother Lodge and Custom Log Cabin With Deck And 45 Acres By Pine River will make you feel at home.

How far in advance should I book my Osceola County holiday?

Reserving your seat early with Expedia means one less thing to have to worry about. Most air carriers display prices up to a year in advance. This is typically the cheapest time to book. If circumstances have left you booking late, discount tickets to Osceola County sometimes become available just a few weeks before departure.

What does an Expedia Osceola County travel package include?

Flights, car rentals and hotels — we bring you the very best bargains. All you have to do is figure out your preferred combination. After you've made your booking, you can add on the exciting stuff like day tours and sightseeing activities. Our travel packages make it easy to put together an awesome Osceola County trip.

What should I know before booking an Osceola County travel package?

Get ready to save with an Expedia travel package. Bundle your airfares, rental cars and hotels and pick up fabulous discounts. Hotels aren't your only choice, however. Book with us and take your pick of island villas, creek-side mountain cabins and everything in between!

Can I choose my airline with an Osceola County Expedia holiday package?

With a holiday package, you're the boss. Whether you're looking to fly to Osceola County in economy or business class, simply select from the available airline options. Expedia has access to more than 550 airline partners throughout the world.

If I'm not able to travel, can I cancel my Osceola County holiday package?

Because we know life can be unpredictable, the answer is yes. To find out more, check out our Customer Service Portal. But generally speaking, if you've booked your Osceola County holiday package in the last 24 hours, you may be able to cancel or change it for no charge. Your hotel, airline or car rental company may charge a fee if you made your booking a while ago.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.