Osceola Vacations from $312

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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.

The Latest Osceola vacation packages

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 out of 5
Price was $435, price is now $312 per person
$312
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to Minneapolis (MSP)
8.8/10 Excellent! (590 reviews)
We had a one bedroom suite with 2 beds. We had a party of 3. The beds were double beds only and had i been aware of that, i would've continued to look for at least a hotel with queen beds. The room was ok but we had a large AC/heater with venting through the Window area and another tall heater stand in the room. There's a lot of cold air coming in underneath the furnace room door. Front desk staff was wonderful upon check in. That's our main reason for the positives in our stay.

Reviewed on Nov 17, 2025

Nicollet Island Inn

Nicollet Island Inn

2.5 out of 5
Nicollet Island
Save 100% on your flight
Price was $518, price is now $336 per person
$336
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Minneapolis (MSP)
9/10 Wonderful! (52 reviews)
Was surprised at the extra historical charge.

Reviewed on Aug 9, 2025

Radisson Blu Mall of America

Radisson Blu Mall of America

4.5 out of 5
East Bloomington
Save 100% on your flight
Price was $798, price is now $521 per person
$521
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to Minneapolis (MSP)
9/10 Wonderful! (2,648 reviews)
There was no free breakfast option. There is a restaurant that is upscale that has breakfast on the 2nd floor. Otherwise you can walk across the street for an IHOP. Additionally, there is no option to do guest laundry at the hotel. Also, no hot tub at the pool and the heated pool water was freezing cold. Staff was super friendly though.

Reviewed on Dec 24, 2025

Country Inn & Suites by Radisson, Bloomington at Mall of America, MN

Country Inn & Suites by Radisson, Bloomington at Mall of America, MN

3 out of 5
East Bloomington
Save 100% on your flight
Price was $514, price is now $354 per person
$354
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to Minneapolis (MSP)
8.8/10 Excellent! (2,057 reviews)
Hot tub is closed for repairs. We specifically chose this hotel for a hot tub. The front desk told us the hotel manager decided not to put this fact on the website

Reviewed on Dec 25, 2025

Holiday Inn Express & Suites Mall of America - MSP Airport by IHG

Holiday Inn Express & Suites Mall of America - MSP Airport by IHG

2.5 out of 5
East Bloomington
Price was $536, price is now $392 per person
$392
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to Minneapolis (MSP)
9/10 Wonderful! (2,747 reviews)
Rooms were clean and the bed was comfortable. Nice breakfast

Reviewed on Dec 23, 2025

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Discover the most popular places to visit in Osceola

Osceola & St. Croix Valley Railway

Enjoy a stop at Osceola & St. Croix Valley Railway, an entertaining place to visit in Osceola. Discover the waterfalls in this relaxing area.

Osceola & St. Croix Valley Railway

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
$90 nightly
The price is $99 total per night from Jan 1 to Jan 2
$99 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
7.8/10 Good! (424 reviews)
The staff and managers went above and beyond to make our stay easy and warm.

Reviewed on Dec 22, 2025

River Valley Inn & Suites
Hotel Crosby

Hotel Crosby

2.5 out of 5
232 Main St N Stillwater MN
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $215 total per night from Jan 5 to Jan 6
$215 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
9.4/10 Exceptional! (999 reviews)
Fantastic stay. Fun ambience, decorated for the holidays, good restaurant downstairs.

Reviewed on Dec 22, 2025

Hotel Crosby
Best Western Plus White Bear Country Inn

Best Western Plus White Bear Country Inn

3 out of 5
4940 Highway 61 North White Bear Lake MN
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $130 total per night from Dec 28 to Dec 29
$130 total
Dec 28 - Dec 29
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
The staff was amazing! The rooms were clean and the restaurant was really good!

Reviewed on Dec 12, 2025

Best Western Plus White Bear Country Inn
See all 464 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.

Find the Best Osceola Vacation Packages

Osceola Essential Information

Language
English
Currency
U.S dollars
Population
2,500
Max Temp Winter
20ºF
Max Temp Summer
75ºF
Top Sights
Interstate State Park- Wisconsin, Dancing Dragonfly Winery and Fawn Doe Rosa Wildlife Educational Park

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Frequently asked questions

How much does an Osceola vacation package cost?
Offering great value package deals from $312 on Expedia, you'll be thrilled with how little a vacation to Osceola costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Osceola?
You're likely to find lower prices and greater availability in May, June and October. Explore our cheap Osceola vacation packages and you could get some great off-season deals.
How many days is enough for Osceola?
Generally, a handful of days is enough to visit the top sights during your Osceola vacation. However, if you want to have some time to rest or go on day tours, consider extending your trip.
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 entertained. Whether you're traveling with the family or planning a trip with friends, an Osceola vacation promises a good time for everyone.
How to find the best Osceola package deals?
Use Expedia's filters to find some fabulous Osceola package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Osceola package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book an Osceola vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still have the freedom to create a personalized Osceola vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Osceola?
If you have your Osceola vacation dates confirmed, book as soon as you can to bag some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Osceola vacation packages?
Secure your dream trip to Osceola with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait for your next payday — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stay on budget and snap up bargains while they last.

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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.