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.
Hilton Minneapolis/Bloomington

Hilton Minneapolis/Bloomington

4 out of 5
West Bloomington
Price was CA $922, price is now CA $781 per person
CA $781
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Minneapolis (MSP)
9.2/10 Wonderful! (1,007 reviews)
The staff was not friendly.

Reviewed on Jul 6, 2026

The Lofton Hotel, Tapestry Collection by Hilton

The Lofton Hotel, Tapestry Collection by Hilton

4.5 out of 5
Downtown Minneapolis
Price was CA $1,240, price is now CA $997 per person
CA $997
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Minneapolis (MSP)
9.4/10 Exceptional! (1,038 reviews)
Clean room

Reviewed on Jul 5, 2026

Moxy Minneapolis Downtown

Moxy Minneapolis Downtown

3 out of 5
Downtown Minneapolis
Price was CA $1,224, price is now CA $1,013 per person
CA $1,013
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Minneapolis (MSP)
9/10 Wonderful! (889 reviews)
Window in the shower? Not advised. Shower head and wand holder broken.

Reviewed on Jul 5, 2026

The Marquette Hotel, Curio Collection by Hilton

The Marquette Hotel, Curio Collection by Hilton

4 out of 5
Downtown Minneapolis
Price was CA $1,435, price is now CA $1,206 per person
CA $1,206
per person
Sep 11 - Sep 14
found 15 hours ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Minneapolis (MSP)
9.4/10 Exceptional! (1,001 reviews)
The room was very spacious, really well laid out with great storage, lobby had a great vibe and pool table. Everything we needed in a convenient location downtown.

Reviewed on Jul 7, 2026

Hyatt Regency Minneapolis

Hyatt Regency Minneapolis

4 out of 5
Downtown Minneapolis
Price was CA $1,052, price is now CA $899 per person
CA $899
per person
Sep 7 - Sep 11
found 5 hours ago
Roundtrip flight included
Saskatoon (YXE) to Minneapolis (MSP)
8.8/10 Excellent! (1,003 reviews)
The staff were amazing. The check in process was seamless and quick, she was super friendly and the rooms were clean. Also we loved the fitness centre it was fantastic!

Reviewed on Jul 1, 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 $136 per night from Jul 19 to Jul 20
CA $136
CA $150 total
Jul 19 - Jul 20
includes taxes & fees
7.8/10 Good! (459 reviews)
"The hotel staff was so helpful and the property was spotless. Location is great with a restaurant next door. We would recommend the River Valley Inn and Suites."

Reviewed on Jun 29, 2026

River Valley Inn & Suites
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 $248 per night from Jul 19 to Jul 20
CA $248
CA $278 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very good! (1,011 reviews)
"Bathroom shower was not cleaned."

Reviewed on Jul 6, 2026

Water Street Inn
Best Western Plus Hudson I-94

Best Western Plus Hudson I-94

2.5 out of 5
1200 Gateway Blvd Hudson WI
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Jul 26 to Jul 27
CA $136
CA $148 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (645 reviews)
"We come to Hudson at least once a year and normally stay at another hotel. However, for this trip we decided to try this hotel. Upon arrival, there was a drink in the fridge, some type of substance on the air conditioning unit, and hair throughout the shower. Thankfully, once calling down to the ..."

Reviewed on Jul 6, 2026

Best Western Plus Hudson I-94
See all 479 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 $781 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.