Osceola Vacations from $274

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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.
Hilton Minneapolis

Hilton Minneapolis

4 out of 5
Downtown Minneapolis
Save 100% on your flight
Price was $444, price is now $274 per person
$274
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Minneapolis (MSP)
8.8/10 Excellent! (1,013 reviews)
Friendly staff, really easy to get late checkout

Reviewed on Oct 30, 2025

Nicollet Island Inn

Nicollet Island Inn

2.5 out of 5
Nicollet Island
Save 100% on your flight
Price was $573, price is now $377 per person
$377
per person
Jan 5 - Jan 8
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Minneapolis (MSP)
9/10 Wonderful! (50 reviews)
Was surprised at the extra historical charge.

Reviewed on Aug 9, 2025

Graduate by Hilton Minneapolis

Graduate by Hilton Minneapolis

4 out of 5
Dinkytown
Price was $488, price is now $347 per person
$347
per person
Jan 5 - Jan 8
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Minneapolis (MSP)
9.2/10 Wonderful! (1,022 reviews)
The breakfast food was very fresh and delicious. The dinner menu was great. Bed super comfy, room very clean. Staff very friendly and attentive.

Reviewed on Nov 1, 2025

Radisson RED Minneapolis Downtown

Radisson RED Minneapolis Downtown

3.5 out of 5
Downtown Minneapolis
Save 100% on your flight
Price was $520, price is now $383 per person
$383
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Minneapolis (MSP)
8.6/10 Excellent! (1,017 reviews)
Conveniently located near US Bank Stadium, our true destination. Very clean and modern. We did not use any of the facilities.

Reviewed on Oct 23, 2025

The Westin Minneapolis

The Westin Minneapolis

4 out of 5
Downtown Minneapolis
Price was $453, price is now $336 per person
$336
per person
Jan 5 - Jan 8
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Minneapolis (MSP)
8.2/10 Very Good! (1,006 reviews)
Great value, and the restaurant is amazing!

Reviewed on Oct 29, 2025

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Discover the most popular places to visit in Osceola

Osceola & St. Croix Valley Railway

5/5(1 review)

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
$100 nightly
The price is $110 total per night from Nov 4 to Nov 5
$110 total
Nov 4 - Nov 5
Total with taxes and fees
7.8/10 Good! (418 reviews)
Yes

Reviewed on Oct 17, 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
$197 nightly
The price is $221 total per night from Nov 16 to Nov 17
$221 total
Nov 16 - Nov 17
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
Beautiful hotel with comfy, clean quiet room, wonderful service, great restaurant and bar.

Reviewed on Oct 28, 2025

Hotel Crosby
Country Inn & Suites by Radisson, Forest Lake, MN

Country Inn & Suites by Radisson, Forest Lake, MN

2.5 out of 5
1954 West Broadway Avenue, Forest Lake, MN
Fully refundable
$77 nightly
The price is $83 total per night from Nov 30 to Dec 1
$83 total
Nov 30 - Dec 1
Total with taxes and fees
7.8/10 Good! (870 reviews)
Better breakfast items would have been great. Way to many things full of just carbohydrates

Reviewed on Oct 23, 2025

Country Inn & Suites by Radisson, Forest Lake, MN
See all 461 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 $274 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.

Explore a world of travel with Expedia

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