Osceola Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit

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

Osceola Holiday

Our pick of the best Osceola Hotel Deals

River Valley Inn & Suites
River Valley Inn & Suites
2.5 out of 5
1030 N Cascade Street, Osceola, WI
Fully refundableReserve now, pay when you stay
The price is NZ$182 per night from 27 July to 28 July
NZ$182
27 July - 28 July
includes taxes & fees
7.8/10 Good! (394 reviews)
"Property is clean, quiet and well maintained. I have stayed here before."

Reviewed on 14 Jun. 2025

River Valley Inn & Suites
Hudson Inn & Suites
Hudson Inn & Suites
3 out of 5
811 Dominion Drive, Hudson, WI
Fully refundableReserve now, pay when you stay
The price is NZ$146 per night from 14 July to 15 July
NZ$146
14 July - 15 July
includes taxes & fees
8.2/10 Very Good! (724 reviews)
Good place for an evening stay
"Good place to stop for a nights stay Friendly greeting from employee Nice room I would go there again"

Reviewed on 29 Jun. 2025

Hudson Inn & Suites
Hotel Crosby
Hotel Crosby
2.5 out of 5
232 Main St N, Stillwater, MN
The price is NZ$475 per night from 30 July to 31 July
NZ$475
30 July - 31 July
includes taxes & fees
9.4/10 Exceptional! (927 reviews)
"Amazing stay and great staff."

Reviewed on 11 Jul. 2025

Hotel Crosby
See all 463 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?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Osceola costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Osceola?
October, November and December are great times to search for cheap Osceola holiday packages. Opting to travel in quieter months means you can generally find lower prices on flights and hotels.
How many days is enough for Osceola?
With a well-organised schedule, you can easily tick off the most popular Osceola sights in a handful of days. But if you want to venture off the beaten track or take day trips, think about booking your Osceola holiday for longer.
Is it worth booking a holiday package to Osceola?
It's easy to see why an Osceola holiday is on the to-do list of many travellers. Popular attractions like Osceola & St. Croix Valley Railway are just the beginning of what you can explore here.
How to find the best Osceola package deals?
Use Expedia's filters to find some fabulous Osceola package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Osceola package deals in the off-peak 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?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still have the freedom to create a personalised Osceola holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Osceola?
If you have your Osceola holiday dates confirmed, book as soon as you can to bag some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Osceola?

  1. Pick your travel dates: What you plan to do in Osceola and your favourite season can help you decide when to get away.
  2. Budget wisely: Besides the cost of your stay, you'll need to consider other expenses. These include flights, food and transportation. Also, set aside a little extra for unexpected costs that may arise during your trip to Osceola.
  3. Set the duration of your trip: Start by making a list of all the attractions you want to get to in Osceola. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find an Osceola holiday package that brings all your bookings together.

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