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.
Four Seasons Hotel Minneapolis
Downtown Minneapolis
CA $1,935
per person
Nov 6 - Nov 10
found 17 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Minneapolis (MSP)
9.6/10 Exceptional! (350 reviews)
The Four Season is the best of the best. No other hotel comes close to their attention to detail.
Reviewed on Aug 24, 2026
Hyatt Regency Minneapolis
Downtown Minneapolis
CA $1,228
per person
Nov 6 - Nov 10
found 17 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Minneapolis (MSP)
9/10 Wonderful! (1,005 reviews)
This is my second time staying at the Hyatt Regency Nicolett Mall in Minneapolis. The front desk (Fatima) was wonderful. She helped me solve the parking issue, introduced me to Hyatt rewards at the hotel, explained the breakfast package better (which had not been explained at my prior visit) and made the experience great overall. The service at the restaurant was okay. Dinner service was not great as there were waiters standing around before we got served. The buffet was great and breakfast service was much better. The service at the market was excellent. Room service was not great. There were few supplies in the bathroom (toilet tissue, towels) for three people in the room. I left multiple messages Saturday night and no one ever responded. The first time was better. This time was mediocre. But since it is close to my son's college and we will likely be traveling back to Minneapolis soon, I'd stay here again.
Reviewed on Aug 24, 2026
Ready to book your vacation to Osceola?
Osceola Hotel Deals
River Valley Inn & Suites
1030 N Cascade Street Osceola WI
Fully refundableReserve now, pay when you stay
CA $109
CA $120 total
Aug 25 - Aug 26
includes taxes & fees
7.8/10 Good! (490 reviews)
"hot tube didnt work and ther was no way to turn jets on"
Reviewed on Aug 24, 2026
Water Street Inn
101 Water St South Stillwater MN
Fully refundableReserve now, pay when you stay
CA $178
CA $199 total
Aug 25 - Aug 26
includes taxes & fees
8.2/10 Very good! (1,015 reviews)
"The hotel itself was well maintained on the outside and the appearance when you walk in is very nice. I feel like my room was back in an older part of the building where nothing was updated. The door wouldn't shut all the way on its own so it didnt lock unless you pulled it shut... I guess I had ..."
Reviewed on Aug 24, 2026
Best Western Plus White Bear Country Inn
4940 Highway 61 North White Bear Lake MN
Fully refundableReserve now, pay when you stay
CA $169
CA $184 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
"Best place I have stayed while traveling. Owner is normally on site and resturuant and bar are 5 star as well."
Reviewed on Aug 24, 2026
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.
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.
Farmington Bottoms State Natural Area
Explore the great outdoors at Farmington Bottoms State Natural Area, a lovely green space in Osceola. Take in the entertainment venues and waterfalls in the area.
Rice Lake
Commune with nature and explore the great outdoors at Rice Lake during your travels in Osceola. Amble around the area's riverfront or experience its entertainment venues.
Riverwood Canoe
8.0/10 (6 reviews)
You can take time to visit Riverwood Canoe during your travels to Osceola. Discover the waterfalls in this relaxing area.
Big Lake
Commune with nature and explore the great outdoors at Big Lake during your travels in Osceola. Take in the entertainment venues and waterfalls in the area.
Church Pine Lake
Commune with nature and explore the great outdoors at Church Pine Lake during your travels in Osceola. Wander the riverfront or discover the area's waterfalls.
Frequently asked questions
How much does an Osceola vacation package cost?
You can pick up a vacation package to this popular destination from CA $990 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?
- 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.
- 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.
- 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.
- 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.
