Osceola Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Kelly Lasswell

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

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

Your Osceola Vacation

Choose a Osceola vacation package and concentrate on what matters — having some fun. There's no more planning hassles, just a lot more time to uncover the best parts of this lively city, such as its rich history and friendly locals. A trip to Osceola wouldn't be complete without checking out a few top attractions, like Osceola Cheese. Your dream Osceola vacation is a few clicks away. Browse hotels, flights and more on Expedia for a getaway that's tailored to suit your travel style.

Top Osceola Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hawthorne Inn

Hawthorne Inn

2 out of 5
Price was CA $1,317, price is now CA $1,270 per person
CA $1,270
per person
Nov 2 - Nov 7
found 16 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Versailles (VRS)
9.2/10 Wonderful! (47 reviews)
A beautiful home with a history. Very clean and well kept. A wonderful home cooked breakfast. I would definitely recommend.

Reviewed on Feb. 26, 2025

Coconuts RV Resort

Coconuts RV Resort

2 out of 5
Price was CA $1,710, price is now CA $1,411 per person
CA $1,411
per person
Nov 2 - Nov 7
found 16 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Versailles (VRS)
10/10 Exceptional! (2 reviews)
Had a blast! The pool staff were all amazing and friendly. We stayed at one of the villas with my family of five. It was perfect for our annual family vacation.

Reviewed on Jul. 19, 2025

Lake It Easy - Waterfront Getaway With 7 Bedrooms!

Lake It Easy - Waterfront Getaway With 7 Bedrooms!

4 out of 5
Price was CA $3,488, price is now CA $3,281 per person
CA $3,281
per person
Nov 2 - Nov 7
found 16 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Versailles (VRS)
No reviews
Panoramic Paradise - Lakefront Home for 15

Panoramic Paradise - Lakefront Home for 15

4.5 out of 5
Price was CA $3,768, price is now CA $3,548 per person
CA $3,548
per person
Nov 2 - Nov 7
found 16 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Versailles (VRS)
No reviews
Sunsets at Washburn

Sunsets at Washburn

3.5 out of 5
Price was CA $2,186, price is now CA $2,086 per person
CA $2,086
per person
Nov 2 - Nov 7
found 16 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Versailles (VRS)
No reviews

Ready to book your vacation to Osceola?

 

Choose your dates

Osceola Hotel Deals

Postcard Cabins Ozark Highlands

Postcard Cabins Ozark Highlands

2 out of 5
11750 NE 230 Rd, Osceola, MO
The price is CA $123 per night from Sep 1 to Sep 2
CA $123
CA $179 total
Sep 1 - Sep 2
includes taxes & fees
9.8/10 Exceptional! (19 reviews)
"When I first arrived the bed was covered in dead flies and mouse feces. I asked for a new cabin but they came and changed the sheets for us. as we waited outside in the heat. I just expected it to be cleaner."

Reviewed on Aug. 18, 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 CA $161 per night from Sep 8 to Sep 9
CA $161
CA $267 total
Sep 8 - Sep 9
includes taxes & fees
10/10 Exceptional! (13 reviews)
"The cabin is located at the end of a gravel road. It is very quiet and peaceful. The screened porch is an added bonus. The cabin is very clean and well maintained. This is our second stay and look forward to renting it next summer."

Reviewed on Aug. 5, 2025

Secluded Hunting & Fishing cabin in the Woods - Osceola, MO
Westbridge Inn and Suites

Westbridge Inn and Suites

2 out of 5
106 S Baird St., Clinton, MO
Fully refundableReserve now, pay when you stay
The price is CA $88 per night from Aug 31 to Sep 1
CA $88
CA $105 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very Good! (656 reviews)
"Clean complex. Older motel but well kept. Friendly staff"

Reviewed on Aug. 19, 2025

Westbridge Inn and Suites
See all 228 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Osceola vacation package cost?
You'll find cheap prices from CA $1,270 on Expedia for your Osceola getaway. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Osceola costs.
What are the cheapest months to go to Osceola?
To pick up cheap Osceola vacation packages, plan your trip outside of busy periods such as school holidays. You'll typically find better availability and lower prices for hotels and flights.
How many days is enough for Osceola?
Typically, a handful of days is enough to go to the top attractions during your Osceola vacation. However, if you'd like to have more time to chill out or take day trips, think about extending your trip.
How to find the best Osceola package deals?
Begin your search for an Osceola package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Osceola package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Osceola escape off to a flying start.
Is it cheaper to book an Osceola vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component separately. And you'll still have the flexibility to create a customized Osceola vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Osceola?
If you've got your Osceola vacation dates confirmed, book as soon as you can to bag some outstanding deals. With Expedia, you can generally reserve some flights up to one year in advance. 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 calendar and pack your bags. Your preferred season and the type of activities available will also help you decide when to visit Osceola.
  2. Calculate your budget: Make sure you have enough money to pay for everything from meals and transportation to activities and flights. Your hotel will probably be the largest expense during your trip to Osceola.
  3. Decide how long to go for: Now that you're more familiar with Osceola, you can work out the perfect length of your vacation. Put together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to pick 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.