Osceola Vacations from $588

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The Latest Osceola vacation packages

Price found within the past 48 hours. Click for updated prices.
Vinehurst Inn And Suites

Vinehurst Inn And Suites

2.5 out of 5
Price was $611, price is now $588 per person
$588
per person
Jul 16 - Jul 19
found 13 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Elmira (ELM)
8.8/10 Excellent! (651 reviews)
This stay EXCEEDED all my expectations!! The wonderful host who checked us is was so very nice to deal with! She took care of everything we needed! Restaurant recommendations, early check in and had a wonderful breakfast ready for all the guests! We will be back!!

Reviewed on May 18, 2026

Staybridge Suites Corning by IHG

Staybridge Suites Corning by IHG

3 out of 5
Price was $797, price is now $734 per person
$734
per person
Jul 16 - Jul 19
found 13 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Elmira (ELM)
9.2/10 Wonderful! (1,002 reviews)
It was very nice, and the stuff was helpful. We would book from this hotel again.

Reviewed on Apr 27, 2026

Best Western Plus The Hammondsport Hotel

Best Western Plus The Hammondsport Hotel

2.5 out of 5
Price was $732, price is now $703 per person
$703
per person
Jul 16 - Jul 19
found 13 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Elmira (ELM)
9.6/10 Exceptional! (1,006 reviews)
Breakfast was okay. The front desk clerk was also the person taking care of the breakfast room. So maybe they are a little short staffed. The mattress was horrible for me. I can’t see myself staying here again because of this.

Reviewed on May 19, 2026

Radisson Hotel Corning

Radisson Hotel Corning

3.5 out of 5
Gaffer District
Price was $701, price is now $679 per person
$679
per person
Jul 16 - Jul 19
found 13 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Elmira (ELM)
8.8/10 Excellent! (1,126 reviews)
Room was clean, staff was great. Our only negatives were there was no microwave or pod-friendly coffee maker.

Reviewed on May 19, 2026

The Oak & Anchor Inn

The Oak & Anchor Inn

2 out of 5
Price was $693, price is now $632 per person
$632
per person
Jul 16 - Jul 18
found 13 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Elmira (ELM)
10/10 Exceptional! (1 review)
Serene and utterly charming. Julie is a fabulous hostess and a great cook!

Reviewed on May 16, 2026

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Osceola Hotel Deals

Radisson Hotel Corning

Radisson Hotel Corning

3.5 out of 5
125 Denison Pkwy E Corning NY
Fully refundable
$111 nightly
The price is $124 total per night from Jun 21 to Jun 22
$124 total
Jun 21 - Jun 22
Total with taxes and fees
8.8/10 Excellent! (1,136 reviews)
"The room was spacious & clean, the bed was a bit uncomfortable but I'm spoiled with a premium set up at home. Very quiet, walking distance to the shops & museums."

Reviewed on May 21, 2026

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
$78 nightly
The price is $88 total per night from May 29 to May 30
$88 total
May 29 - May 30
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
"quick stopover on a road trip. super friendly. clean and quiet. older but reasonably maintained great for the price."

Reviewed on May 21, 2026

Americas Best Value Inn Painted Post
Hilton Garden Inn Corning Downtown

Hilton Garden Inn Corning Downtown

3 out of 5
23 Riverside Dr Corning NY
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $155 total per night from May 31 to Jun 1
$155 total
May 31 - Jun 1
Total with taxes and fees
9.6/10 Exceptional! (1,001 reviews)
"All staff were very welcoming, helpful and professional. Front desk staff were very helpful with answering questions and providing information about the local area."

Reviewed on May 4, 2026

Hilton Garden Inn Corning Downtown
See all 323 properties in Osceola
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.

Find the Best Osceola Vacation Packages

Osceola Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Elmira - Corning Regional Airport (ELM)

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Frequently asked questions

How much does an Osceola vacation package cost?
Offering excellent value package deals from $588 on Expedia, you'll be pleasantly surprised at how much a vacation to Osceola costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Osceola?
You can usually find lower rates and greater availability in November, December and January. Take a look at our cheap Osceola vacation packages and you could land some great off-season deals.
How many days is enough for Osceola?
With a well-organized itinerary, you can easily visit the most popular Osceola sights in a handful of days. But if you want to discover hidden gems or go on day tours, consider booking your Osceola vacation 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 vacation package as soon as possible.
Is it cheaper to book an Osceola vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays separately. Better still, you can customize 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 vacation 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.
Does Expedia offer Book Now, Pay Later Osceola vacation packages?
If you're like us, you love traveling but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Osceola vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.