Osceola Vacations from $629

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Your Osceola Vacation

Uncover the best of Osceola with a tailor-made Osceola vacation package. From its small-town feel and friendly locals to its rich history, you'll love discovering this riverfront city in the way that you want. If visiting the sights is a priority during your trip to Osceola, make sure you find your way to popular attractions like Osceola & St. Croix Valley Railway and Riverwood Canoe. Expedia has what you need to escape your routine. Tailor your vacation to Osceola to suit your style of travel, whatever that may be.

The Latest Osceola vacation packages

Price found within the past 48 hours. Click for updated prices.
Mystic Lake Casino Hotel

Mystic Lake Casino Hotel

3.5 out of 5
Price was $785, price is now $629 per person
$629
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Minneapolis (MSP)
9/10 Wonderful! (2,534 reviews)
BathRoom was smallerthen expected

Reviewed on May 7, 2026

Nicollet Island Inn

Nicollet Island Inn

2.5 out of 5
Nicollet Island
Price was $1,110, price is now $837 per person
$837
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip flight included
Mesa (AZA) to Minneapolis (MSP)
9/10 Wonderful! (73 reviews)
The hotel was in a great location with easy access to downtown. Great parking with equally helpful staff.

Reviewed on May 5, 2026

Hotel Crosby

Hotel Crosby

2.5 out of 5
Save 100% on your flight
Price was $1,562, price is now $1,182 per person
$1,182
per person
Jun 30 - Jul 5
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Minneapolis (MSP)
9.6/10 Exceptional! (1,006 reviews)
Very nice rooftop sitting area and hot tub! Matchstick restaurant with great reviews. Just wish they served breakfast-at least on the weekends. Very good customer service by all staff!

Reviewed on May 9, 2026

Moxy Minneapolis Downtown

Moxy Minneapolis Downtown

3 out of 5
Downtown Minneapolis
Price was $891, price is now $693 per person
$693
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip flight included
Mesa (AZA) to Minneapolis (MSP)
9/10 Wonderful! (854 reviews)
Excellent location - very nice staff - fantastic bar. The ONLY downside is their weird bathroom set up. Why have a window in the shower that looks out to the bed? More importantly, WHY is there an automatic light in the bathroom? So when a person gets up at 2am to use the restroom, the light automatically comes on, and then the partner that is in the bed gets woken up by the light. This makes no sense. Other than this annoyance, everything else was great.

Reviewed on May 8, 2026

Emery, Autograph Collection Hotel

Emery, Autograph Collection Hotel

4.5 out of 5
Downtown Minneapolis
Price was $962, price is now $750 per person
$750
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Minneapolis (MSP)
9.2/10 Wonderful! (697 reviews)
The Spyhouse Coffee House on the first floor is worth the stay. The restaurant bar was fantastic. The location is perfect for walking to the North Loop, Washington Ave., the theaters, US Bank Stadium - you name it!

Reviewed on May 5, 2026

Don't see what you're looking for?
See all available trips from Columbus to Osceola
View all trips

Discover the most popular places to visit in Osceola

Osceola & St. Croix Valley Railway

Enjoy a stop at Osceola & St. Croix Valley Railway, an entertaining place to visit in Osceola. Discover the waterfalls in this relaxing area.

Osceola & St. Croix Valley Railway

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
$95 nightly
The price is $105 total per night from May 14 to May 15
$105 total
May 14 - May 15
Total with taxes and fees
7.8/10 Good! (442 reviews)
The room was clean. I had to plug everything in when I arrived. I was so excited to go sit in the hot tub after my long trip only to discover it hadn’t worked in over 2 years! Very disappointing so if that is a must for you, don’t book this hotel. The free breakfast was a bunch of cereal that looked ...

Reviewed on May 9, 2026

River Valley Inn & Suites
Hotel Crosby

Hotel Crosby

2.5 out of 5
232 Main St N Stillwater MN
Fully refundableReserve now, pay when you stay
$224 nightly
The price is $251 total per night from May 26 to May 27
$251 total
May 26 - May 27
Total with taxes and fees
9.6/10 Exceptional! (1,012 reviews)
The room was clean and spacious. I wish there would have been a closet. They did give us a bottle of wine for our anniversary.

Reviewed on May 11, 2026

Hotel Crosby
Water Street Inn

Water Street Inn

3.5 out of 5
101 Water St South Stillwater MN
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $151 total per night from May 13 to May 14
$151 total
May 13 - May 14
Total with taxes and fees
8.2/10 Very Good! (994 reviews)
great staff

Reviewed on May 11, 2026

Water Street Inn
See all 473 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.

Find the Best Osceola Vacation Packages

Osceola Essential Information

Language
English
Currency
U.S dollars
Population
2,500
Max Temp Winter
20ºF
Max Temp Summer
75ºF
Top Sights
Interstate State Park- Wisconsin, Dancing Dragonfly Winery and Fawn Doe Rosa Wildlife Educational Park

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Osceola vacation package cost?
Offering great value package deals from $629 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?
You're likely to find lower prices and greater availability in May, June and October. Explore our cheap Osceola vacation packages and you could get some great off-season deals.
How many days is enough for Osceola?
Generally, a handful of days is enough to visit the top sights during your Osceola vacation. However, if you want to have some time to rest or go on day tours, consider extending your trip.
Is it worth booking a vacation package to Osceola?
Osceola is a good vacation destination with attractions like Osceola & St. Croix Valley Railway among the many things to keep you entertained. Whether you're traveling with the family or planning a trip with friends, an Osceola vacation promises a good time for everyone.
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.
Does Expedia offer Book Now, Pay Later Osceola vacation packages?
Secure your dream trip to Osceola with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait for your next payday — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stay on budget and snap up bargains while they last.

Explore a world of travel with Expedia

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