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.
Candlewood Suites Eagan Arpt South - Mall Area by IHG

Candlewood Suites Eagan Arpt South - Mall Area by IHG

3.5 out of 5
Price was CA $873, price is now CA $764 per person
CA $764
per person
Aug 6 - Aug 9
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Minneapolis (MSP)
8.8/10 Excellent! (625 reviews)
Clean, peaceful, and quiet on a Friday/Saturday. Pristine pool and hot tub, which we had all to ourselves both times we visited. Make sure to have brunch at the nearby Southern Social if you are there on a weekend.

Reviewed on Jul 2, 2026

Emery, Autograph Collection Hotel

Emery, Autograph Collection Hotel

4.5 out of 5
Downtown Minneapolis
Price was CA $1,164, price is now CA $905 per person
CA $905
per person
Aug 17 - Aug 20
found 15 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Minneapolis (MSP)
9.2/10 Wonderful! (740 reviews)
The room was thoughtfully designed for a small room and was beautifully decorated. The onsite gym was well equipped and spacious. The bar/restaurant was delicious and well staffed. Only complaint, offsite self parking was a bit challenging, it was close but getting in and out of the garage on weekend required assistance from human versus automatic.

Reviewed on Jul 1, 2026

Cambria Hotel Bloomington Mall of America Minneapolis Airport

Cambria Hotel Bloomington Mall of America Minneapolis Airport

3 out of 5
East Bloomington
Price was CA $1,007, price is now CA $860 per person
CA $860
per person
Aug 6 - Aug 9
found 6 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Minneapolis (MSP)
9.4/10 Exceptional! (1,514 reviews)
Staff friendly and efficient. Shuttle service worked well. Food delicious. Clean, spacious and modern room.

Reviewed on Jun 30, 2026

Hotel Indigo Minneapolis Downtown by IHG

Hotel Indigo Minneapolis Downtown by IHG

3.5 out of 5
Downtown Minneapolis
Price was CA $1,286, price is now CA $1,110 per person
CA $1,110
per person
Sep 11 - Sep 14
found 5 hours ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Minneapolis (MSP)
9.4/10 Exceptional! (1,000 reviews)
Clean

Reviewed on Jul 2, 2026

The Marquette Hotel, Curio Collection by Hilton

The Marquette Hotel, Curio Collection by Hilton

4 out of 5
Downtown Minneapolis
Price was CA $932, price is now CA $817 per person
CA $817
per person
Aug 17 - Aug 20
found 15 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Minneapolis (MSP)
9.4/10 Exceptional! (1,003 reviews)

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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 $131 per night from Jul 6 to Jul 7
CA $131
CA $144 total
Jul 6 - Jul 7
includes taxes & fees
7.8/10 Good! (458 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
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 $226 per night from Jul 6 to Jul 7
CA $226
CA $253 total
Jul 6 - Jul 7
includes taxes & fees
8.2/10 Very good! (1,003 reviews)
"Welcoming and friendly staff. Enjoyed delicious food at Charlie's and Papa's rooftop restaurants. Loved the location!"

Reviewed on Jul 2, 2026

Water Street Inn
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 $764 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.