Osceola Vacations from $290
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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.
Stay near popular Osceola attractions
Osceola & St. Croix Valley Railway
8.6/10 (14 reviews)
Journey through the St. Croix River Valley on vintage railcars with the Osceola Railway. Fall excursions showcase spectacular foliage while you experience the charm of historic rail travel.
Farmington Bottoms State Natural Area
This pristine floodplain forest along the St. Croix River offers an untouched wilderness experience amid old-growth trees. Bring a compass to navigate while spotting bald eagles and rare wildflowers.
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)
Glide through the St. Croix River's pristine waters on a 7-mile scenic paddle suitable for all skill levels. Morning trips offer the calmest conditions and best wildlife viewing opportunities.
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.
Osceola Hotel Deals
River Valley Inn & Suites
1030 N Cascade Street Osceola WI
Fully refundableReserve now, pay when you stay
$88 nightly
$97 total
Sep 29 - Sep 30
Total with taxes and fees
7.8/10 Good! (508 reviews)
"on second day, our key card didn't work. we had to get another. carpet in our room was quite stained. gping back a bit, we were charged a $50 deposit fee. is this normal? also, this morning upon wake up, our tv didnt work. stated no service?"
Reviewed on Sep 26, 2026
Historic 1880s Home
Osceola WI
$199 nightly
$220 total
Oct 6 - Oct 7
Total with taxes and fees
10/10 Exceptional! (84 reviews)
"We loved the location as it was near all the sites we wanted to attend. It was within walking distance to the downtown and the falls. The house was great for the five of us. The kids liked the large variety of games available in the house."
Reviewed on Sep 23, 2026
Water Street Inn
101 Water St South Stillwater MN
Fully refundableReserve now, pay when you stay
$130 nightly
$145 total
Sep 29 - Sep 30
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
"Great location but out dated and worn. Staff was friendly and helpful but the carpet throughout hotel and our room was not clean and old."
Reviewed on Sep 27, 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.
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 $290 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.
