Osceola Vacation Packages

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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.

Top Osceola Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hampton Inn by Hilton Minneapolis/Eagan

Hampton Inn by Hilton Minneapolis/Eagan

2.5 out of 5
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip flight included
Regina (YQR) to Minneapolis (MSP)
8.8/10 Excellent! (1,001 reviews)
The staff was exemplary, even offering to pay for an Uber since their van doesn’t run late enough to pick up after the ballgame, and were concerned because our mother was in a wheelchair.

Reviewed on Jul. 11, 2025

Renaissance Minneapolis Hotel, The Depot

Renaissance Minneapolis Hotel, The Depot

4 out of 5
Downtown Minneapolis
Save 100% on your flight
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip flight included
Regina (YQR) to Minneapolis (MSP)
9/10 Wonderful! (997 reviews)
My only complaint is no hot tub and the shower had a weird constant squeaking noise. Otherwise 10/10 would stay again.

Reviewed on Jul. 14, 2025

Radisson Blu Mall of America

Radisson Blu Mall of America

4.5 out of 5
East Bloomington
Save 100% on your flight
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip flight included
Regina (YQR) to Minneapolis (MSP)
9/10 Wonderful! (2,350 reviews)
Great location to MOA. Nice airport shuttle, pool, and daily water bottles.

Reviewed on Jul. 14, 2025

Hyatt House Mall Of America Msp Airport

Hyatt House Mall Of America Msp Airport

2.5 out of 5
East Bloomington
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip flight included
Regina (YQR) to Minneapolis (MSP)
8.6/10 Excellent! (1,321 reviews)
It is a new location

Reviewed on Jul. 14, 2025

Great Wolf Lodge Bloomington

Great Wolf Lodge Bloomington

3 out of 5
East Bloomington
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip flight included
Regina (YQR) to Minneapolis (MSP)
8.4/10 Very Good! (1,007 reviews)
it was really good !! , but there black stuff on some of the beds

Reviewed on Jul. 14, 2025

Ready to book your vacation to Osceola?

 

Choose your dates

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 CA $136 per night from Jul 21 to Jul 22
CA $136
CA $150 total
Jul 21 - Jul 22
includes taxes & fees
7.8/10 Good! (394 reviews)
"Property is clean, quiet and well maintained. I have stayed here before."

Reviewed on Jun. 14, 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 CA $101 per night from Jul 16 to Jul 17
CA $101
CA $120 total
Jul 16 - Jul 17
includes taxes & fees
8.2/10 Very Good! (725 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 Jun. 29, 2025

Hudson Inn & Suites
Hotel Crosby
Hotel Crosby
2.5 out of 5
232 Main St N, Stillwater, MN
The price is CA $356 per night from Jul 30 to Jul 31
CA $356
CA $398 total
Jul 30 - Jul 31
includes taxes & fees
9.4/10 Exceptional! (929 reviews)
Loved it!!
"Loved the room especially kitchenette!!!"

Reviewed on Jul. 11, 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.

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 can pick up a vacation package to this popular destination from CA $499 on Expedia. However, how much your vacation to Osceola costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Osceola?
October, November and December are the best times to look for cheap Osceola vacation packages. Opting to travel in less busy months means you can generally find better prices on flights and accommodations.
How many days is enough for Osceola?
The ideal duration for your Osceola vacation depends on what you'd like to see and do. Typically, a few days to a week will give you plenty of time to check out all the leading attractions and discover some hidden gems along the way.
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 busy. Whether you're travelling with the family or getting away with friends, an Osceola vacation promises a good time for everyone.
How to find the best Osceola package deals?
Use Expedia's filters to help you find some tempting Osceola package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Osceola package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
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 generally score a better deal than booking each component separately. And you'll still have the freedom to create a customized Osceola vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Osceola?
Secure amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Osceola vacation.
How to plan a trip to Osceola?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on 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 airfares. Your hotel will likely be the biggest expense during your trip to Osceola.
  3. Decide how long to go for: Now that you're up to speed on Osceola, you can figure out the right length of your vacation. Put together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Osceola vacation package.

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