Osceola Holidays

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Top hotels in Osceola

Scenic Deck & Grill: Middlebury Center Retreat!

Scenic Deck & Grill: Middlebury Center Retreat!

3 out of 5
Osceola
"Had a great time."

Reviewed on 1 Oct, 2024

Scenic Deck & Grill: Middlebury Center Retreat!
Radisson Hotel Corning

Radisson Hotel Corning

3.5 out of 5
125 Denison Pkwy E, Corning, NY
Fully refundable
The price is S$182 per night from 17 Aug to 18 Aug
S$182
17 Aug - 18 Aug
includes taxes & fees
8.2/10 Very Good! (1,021 reviews)
"I would like to know what decides if you stay in the main hotel or yhe annex building behind the hotel. We stayed in the annex building. Room eas nice, clean and big. However our door would stick and had a hard time entering. The shower doors did not stay closed."

Reviewed on 16 Jul, 2025

Radisson Hotel Corning
Americas Best Value Inn Painted Post

Americas Best Value Inn Painted Post

2 out of 5
196 South Hamilton St., Painted Post, NY
Fully refundableReserve now, pay when you stay
The price is S$116 per night from 31 Jul to 1 Aug
S$116
31 Jul - 1 Aug
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"I like that the staff was very helpful, I also liked the "village" feel that the property offers, Work needs to be done and more cleaning throughout the property including the ice machine."

Reviewed on 15 Jul, 2025

Americas Best Value Inn Painted Post
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 holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Osceola costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Osceola?
The off-season is the best time to head to Osceola if you're trying to keep costs down. Another tip for getting cheap Osceola holiday packages? Try to avoid public holidays and any major festivals.
How many days is enough for Osceola?
With a well-organised travel plan, you can easily visit the top Osceola sights in a few days. But if you want to discover lesser-known spots or go on day tours, think about booking your Osceola holiday for longer.
How to find the best Osceola package deals?
Use Expedia's filters to help you find some tempting Osceola package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Osceola package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your holiday package as soon as possible.
Is it cheaper to book an Osceola holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking flights and stays separately. Better still, you can customise your Osceola escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Osceola?
Score incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Osceola adventure.
How to plan a trip to Osceola?

  1. Choose your travel dates: The things you want to do in Osceola and your favourite season will help you decide when to travel.
  2. Set a budget: Consider expenses such as food, flights and transportation when working out how much to set aside for your trip to Osceola. Then, pick a hotel that works with your budget, whether that's an affordable stay or a swankier getaway.
  3. Decide your trip length: Consider how much time you want to spend exploring Osceola. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a tailored Osceola holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.