Osceola Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to ￥45,448 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
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Find the Best Osceola Vacation Packages

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 ￥14,546 per night from Aug 10 to Aug 11
￥14,546
￥16,073 total
Aug 10 - Aug 11
includes taxes & fees
7.8/10 Good! (397 reviews)
"Friendly and accommodating staff. Beds are very comfortable. Rooms, hallways, etc cleaned very well. Price was great."

Reviewed on Jul 14, 2025

River Valley Inn & Suites
Stillwater Inn & Suites

Stillwater Inn & Suites

2 out of 5
1750 Frontage Rd W, Stillwater, MN
Fully refundableReserve now, pay when you stay
The price is ￥8,875 per night from Aug 17 to Aug 18
￥8,875
￥9,928 total
Aug 17 - Aug 18
includes taxes & fees
6.4/10 (1,002 reviews)
"Decent place"

Reviewed on Aug 4, 2025

Stillwater Inn & Suites
Hotel Crosby

Hotel Crosby

2.5 out of 5
232 Main St N, Stillwater, MN
The price is ￥38,219 per night from Aug 10 to Aug 11
￥38,219
￥42,757 total
Aug 10 - Aug 11
includes taxes & fees
9.4/10 Exceptional! (944 reviews)
"Gorgeous hotel! Free parking was a bonus in a busy walkable area. The rooftop hot tub was clean and large. The restaurant is really good. My only comment would be that the room we were in didnt have an iron."

Reviewed on Aug 4, 2025

Hotel Crosby
See all 449 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 vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation 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 vacation 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-organized 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 vacation for longer.
Is it worth booking a vacation package to Osceola?
It's easy to see why an Osceola vacation is on the to-do list of many travelers. 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 vacation package as soon as possible.
Is it cheaper to book an Osceola vacation as a package?
Expedia vacation 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 personalized Osceola vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Osceola?
If you have your Osceola vacation 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 favorite 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 vacation 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.