How much does an Osceola vacation package cost?

Offering great value package deals from $459 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?

If you're hoping to score a cheap Osceola vacation package, consider planning a trip in February, April and December. You'll usually find lower prices on airfares and hotels during these quieter months — perfect for a budget-friendly getaway.

How many days is enough for Osceola?

The ideal length of your Osceola vacation depends on what you'd like to see. Usually, a handful of days to a week will give you enough time to check out all the main sights and explore some hidden gems along the way.

How to find the best Osceola package deals?

Start your search for an Osceola package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Osceola package deal right away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Osceola adventure underway.

Is it cheaper to book an Osceola vacation as a package?

Expedia vacation 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 typically land a better deal than booking each component separately. And you'll still enjoy the flexibility to create a personalized Osceola vacation by choosing your favorite accommodation type, airline and car class.

When to book a vacation package to Osceola?

Enjoy amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Osceola getaway.

Does Expedia offer Book Now, Pay Later Osceola vacation packages?

Your Osceola trip is meant to be an escape from your daily routine, not a source of money-related stress. So to allow you extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

Osceola Vacation Packages 2025/2026 from $236

Name: Lakeside Hotel Casino
Price range: $103 total
Rating: 8

Your Osceola Vacation

From its small-town feel to its rich history and beyond, there's a whole lot to love about Osceola. Uncover the delights of this awesome city with a Osceola vacation package that's tailored to you. Any trip to Osceola needs a well-thought-out itinerary. Fill yours with major attractions like Lakeside Casino, Osceola Country Club and Clarke County Speedway. Whoever you're taking a break with and whatever the size of your budget, your ultimate Osceola vacation is just a few clicks away with Expedia.

The Latest Osceola vacation packages

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

Colfax Inn

$459

per person

Dec 12 - Dec 15

found 14 hours ago

Roundtrip non-stop flight included

Ontario (ONT) to Des Moines (DSM)

4.8/10 (86 reviews)

Good place clean and quite staff was beyond amazing and very friendly and accommodating

Reviewed on Nov 1, 2025

Cobblestone Inn & Suites - Winterset, IA

$532

per person

Dec 12 - Dec 15

found 14 hours ago

Roundtrip non-stop flight included

Ontario (ONT) to Des Moines (DSM)

9.2/10 Wonderful! (688 reviews)

We found a bug on our bed, it bite Russ.

Reviewed on Nov 5, 2025

Tru By Hilton Grimes Des Moines

$566

per person

Dec 12 - Dec 15

found 14 hours ago

Roundtrip non-stop flight included

Ontario (ONT) to Des Moines (DSM)

8.8/10 Excellent! (6 reviews)

Very noisey PTAC unit for the small size of the room kept me up for 2 nights, won't be staying in this Hilton which is a shame 10 minutes from my daughters. Hiltons are usually my first choice had a better stay 2 weeks ago In Arizona at the Hilton.

Reviewed on Nov 2, 2025

Spark by Hilton Ames

$526

per person

Dec 12 - Dec 15

found 14 hours ago

Roundtrip non-stop flight included

Ontario (ONT) to Des Moines (DSM)

8.8/10 Excellent! (3 reviews)

Clean room nice staff. We would stay again in the future

Reviewed on Nov 3, 2025

Motel 6 Altoona, IA - Des Moines East

$504

per person

Dec 12 - Dec 15

found 14 hours ago

Roundtrip non-stop flight included

Ontario (ONT) to Des Moines (DSM)

6/10 (1,001 reviews)

We just needed a place to shower and sleep that was clean. This fit the bill.

Reviewed on Aug 17, 2025

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Osceola Hotel Deals

Lakeside Hotel Casino

777 Casino Dr, Osceola, IA

Fully refundableReserve now, pay when you stay

$92 nightly

$103 total

Nov 10 - Nov 11

Total with taxes and fees

8/10 Very Good! (1,000 reviews)

Always a great place to stay!

Reviewed on Nov 1, 2025

Super 8 by Wyndham Osceola IA

720 Warren Avenue, I-35 And US-34, Osceola, IA

Fully refundableReserve now, pay when you stay

$83 nightly

$93 total

Nov 9 - Nov 10

Total with taxes and fees

8.6/10 Excellent! (223 reviews)

Very convenient location and wonderful staff!

Reviewed on Oct 12, 2025

Evergreen Inn

221 West McLane (Highway 34), Osceola, IA

Fully refundableReserve now, pay when you stay

$58 nightly

$65 total

Nov 13 - Nov 14

Total with taxes and fees

8.8/10 Excellent! (680 reviews)

The room was clean. When talked to them were very friendly and helpful.

Reviewed on Nov 3, 2025

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.

Things to do in and around Osceola

Osceola, Iowa, offers a delightful mix of romantic and family-friendly activities perfect for a city-themed getaway. Visitors can enjoy scenic spots, relaxing walking trails, and outdoor adventures. Don't miss the local campground for a taste of nature, indulge in rejuvenating body treatments, and explore the shopping mall center for great finds. Whether you're looking for leisurely strolls or exciting activities, Osceola has something for everyone.

Shopping

In Osceola, enjoy local shops like The Quilted Cow for unique gifts and handmade items. If you're up for a drive, visit the Southgate Mall in nearby Des Moines for a wider selection of stores and dining options.

Recreation

Osceola Country Club offers a luxurious retreat with stunning golf courses and upscale amenities, perfect for relaxation and socializing. Little River Recreation Area, located 18 miles away, invites visitors to unwind amidst nature, featuring hiking trails and serene picnic spots. For entertainment, The Winterset Stage provides cultural performances just 25 miles from Osceola.

Adventure

Experience the beauty of the Cinder Path Bike Trail, a scenic hiking trail located 22 miles from Osceola. Enjoy the adventure of biking or hiking through picturesque landscapes, immersing yourself in the great outdoors while soaking in the tranquil vibes of nature.

Nightlife

In Osceola, Iowa, experience a cozy nightlife with local bars and eateries. Visit spots like The Corner Tap for craft beers and live music, or enjoy a relaxed evening at the historic Depot. The town offers a friendly vibe perfect for unwinding after a day of exploration.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Osceola

Osceola, Iowa, offers a charming getaway perfect for romantic couples and families alike, featuring scenic urban parks, picturesque lakes, and serene nature reserves. Visitors can enjoy outdoor experiences that highlight the area's natural beauty, including postcard cabins and breathtaking landscapes. Whether you're seeking a city-themed vacation or a peaceful retreat, Osceola's attractions cater to a variety of interests, ensuring memorable moments for every traveler.

East Lake County Park: This urban park in Osceola offers a family-friendly atmosphere with plenty of outdoor activities. Enjoy scenic walking trails, picnic areas, and playgrounds, making it perfect for a day out with loved ones.
Arbor Valley Lake: Known for its stunning beach and picturesque scenery, Arbor Valley Lake is ideal for a romantic getaway. Relax by the water, take a leisurely stroll along the shoreline, or enjoy water activities in a serene outdoor setting.
West Lake Park: A nature reserve that emphasizes eco-friendly exploration, West Lake Park is perfect for adventure seekers. Discover hiking trails, wildlife watching, and immersive experiences in the great outdoors.

Best time to go to Osceola

The best time to visit Osceola is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly with no rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	22.8°F (-5.1°C)	No Rain	Mostly	Moderately Low	Slightly Low
February	25.3°F (-3.7°C)	No Rain	Mostly Sunny	Moderately Low	Slightly Low
March	40.1°F (4.5°C)	Light Rain	Mostly	Average	Average
April	50.4°F (10.2°C)	Light Rain	Mostly Sunny	Average	Average
May	61.2°F (16.2°C)	Light Rain	Mostly Sunny	Average	Average
June	71.8°F (22.1°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
July	75.0°F (23.9°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
August	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
September	66.9°F (19.4°C)	Light Rain	Mostly Sunny	Average	Average
October	53.2°F (11.8°C)	Light Rain	Mostly Sunny	Average	Average
November	40.6°F (4.8°C)	Light Rain	Mostly Sunny	Average	Average
December	29.8°F (-1.2°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low

Tips to save on your trip to Osceola

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Osceola.
Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Osceola.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Language	English
Currency	U.S dollars
Population	5,000
Max Temp Winter	30ºF
Max Temp Summer	80ºF
Top Sights	Lakeside Casino, Clarke County Speedway and Osceola Country Club

Language

English

Currency

U.S dollars

Population

5,000

Max Temp Winter

30ºF

Max Temp Summer

80ºF

Top Sights

Lakeside Casino, Clarke County Speedway and Osceola Country Club