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.
AC Hotel by Marriott Minneapolis Downtown

AC Hotel by Marriott Minneapolis Downtown

3.5 out of 5
Downtown Minneapolis
Price was CA $1,101, price is now CA $875 per person
CA $875
per person
Aug 20 - Aug 25
found 14 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Minneapolis (MSP)
9.2/10 Wonderful! (1,001 reviews)
Excellent

Reviewed on Jul 4, 2026

Emery, Autograph Collection Hotel

Emery, Autograph Collection Hotel

4.5 out of 5
Downtown Minneapolis
Price was CA $1,454, price is now CA $1,124 per person
CA $1,124
per person
Aug 20 - Aug 25
found 14 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Minneapolis (MSP)
9.2/10 Wonderful! (743 reviews)
The room is clean and quiet, staff friendly.

Reviewed on Jul 7, 2026

Moxy Minneapolis Downtown

Moxy Minneapolis Downtown

3 out of 5
Downtown Minneapolis
Price was CA $1,092, price is now CA $894 per person
CA $894
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Minneapolis (MSP)
9/10 Wonderful! (889 reviews)
It was only myself so the no dresser was perfect. I liked the knobs to hang clothes. It was clean and I loved no carpet. The smell of the hotel was fabulous. I wish they would sell that!

Reviewed on Jul 8, 2026

Embassy Suites by Hilton Minneapolis Downtown

Embassy Suites by Hilton Minneapolis Downtown

4 out of 5
Downtown Minneapolis
Price was CA $1,273, price is now CA $1,054 per person
CA $1,054
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Minneapolis (MSP)
9/10 Wonderful! (1,463 reviews)
Mucho limpio!

Reviewed on Jul 10, 2026

Mystic Lake Casino Hotel

Mystic Lake Casino Hotel

3.5 out of 5
Price was CA $1,273, price is now CA $1,063 per person
CA $1,063
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Regina (YQR) to Minneapolis (MSP)
9/10 Wonderful! (2,611 reviews)
Clean

Reviewed on Jul 9, 2026

Ready to book your vacation to Osceola?

 

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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 $135 per night from Jul 28 to Jul 29
CA $135
CA $150 total
Jul 28 - Jul 29
includes taxes & fees
7.8/10 Good! (462 reviews)
"The one employee was very helpful and very over worked"

Reviewed on Jul 9, 2026

River Valley Inn & Suites
MINNeSTAY* St. Croix Valley Inn

MINNeSTAY* St. Croix Valley Inn

Osceola WI
Get rates
MINNeSTAY* St. Croix Valley Inn
Water Street Inn

Water Street Inn

3.5 out of 5
101 Water St South Stillwater MN
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from Jul 26 to Jul 27
CA $225
CA $252 total
Jul 26 - Jul 27
includes taxes & fees
8.2/10 Very good! (1,013 reviews)
"Convenient location, right downtown. Rooms on river side have views of Lowell Park, St. Croix River and the lift bridge. Rooftop restaurant and the Irish Pub at street level are both good. The rooms are spacious and very clean, comfy mattress and offer a variety of pillows so you can find one that ..."

Reviewed on Jul 7, 2026

Water Street Inn
See all 482 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.
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Stay near popular Osceola attractions

Osceola & St. Croix Valley Railway

8.6/10 (14 reviews)
Enjoy a stop at Osceola & St. Croix Valley Railway, an entertaining place to visit in Osceola. Discover the waterfalls in this relaxing area.
See properties

Frequently asked questions

How much does an Osceola vacation package cost?
You can pick up a vacation package to this popular destination from CA $875 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.

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