Osceola Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Kelly Lasswell

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Osceola Holiday

Our pick of the best Osceola Hotel Deals

Postcard Cabins Ozark Highlands
Postcard Cabins Ozark Highlands
2 out of 5
11750 NE 230 Rd, Osceola, MO
The price is NZ$251 per night from 15 July to 16 July
NZ$251
15 July - 16 July
includes taxes & fees
9.8/10 Exceptional! (12 reviews)
"We spent three nights. It was amazing. Very relaxing. The units were excellent everything furnished, and the few times we needed something the caretakers were with us almost instantly. I would recommend this place to anyone."

Reviewed on 30 Jun. 2025

Postcard Cabins Ozark Highlands
Secluded Hunting & Fishing cabin in the Woods - Osceola, MO
Secluded Hunting & Fishing cabin in the Woods - Osceola, MO
Osceola
The price is NZ$327 per night from 13 July to 14 July
NZ$327
13 July - 14 July
includes taxes & fees
10/10 Exceptional! (13 reviews)
"Great secluded Cabin with all ammenities you need, very clean and well kept would definetly recommend!"

Reviewed on 17 Jun. 2025

Secluded Hunting & Fishing cabin in the Woods - Osceola, MO
The Chestnut on the Square Historic Loft A
The Chestnut on the Square Historic Loft A
Osceola
The price is NZ$282 per night from 16 July to 17 July
NZ$282
16 July - 17 July
includes taxes & fees
Fishing getaway
"Fantastic property close to where we were meeting our fishing guide. This place is a gem tucked on the square in Osceola. Would absolutely stay here again"

Reviewed on 17 Apr. 2025

The Chestnut on the Square Historic Loft A
See all 227 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.

Frequently asked questions

How much does an Osceola holiday package cost?
You'll find cheap prices on Expedia for your Osceola break. However, factors like the length of stay, the season and your choice of hotel will determine how much your holiday to Osceola costs.
What are the cheapest months to go to Osceola?
To pick up cheap Osceola holiday packages, organise your getaway outside of peak times like public holidays and major events. You'll generally find better availability and lower prices for flights and hotels.
How many days is enough for Osceola?
The ideal length of your Osceola holiday depends on what you'd like to see. Generally, a few days to a week will give you enough time to visit all the main attractions and discover some hidden treasures along the way.
How to find the best Osceola package deals?
Start your search for an Osceola package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Osceola package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Osceola getaway off to a flying start.
Is it cheaper to book an Osceola holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still have the flexibility to create a personalised Osceola holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Osceola?
If you've got your Osceola travel dates finalized, book as early as you can to snap up some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Osceola?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to visit Osceola.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and experiences. Your hotel will probably be the largest expense during your trip to Osceola.
  3. Determine how many days away: Start by compiling a list of the activities and attractions you want to get to in Osceola. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customised Osceola holiday package.

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