Osceola Vacations from $306
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Hampton Inn Minneapolis/St. Paul-Woodbury
$423
per person
Sep 21 - Sep 27
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Minneapolis (MSP)
8/10 Very Good! (1,002 reviews)
The girls working the desk were very nice and helpful, but the gym is really limited (even for a hotel gym) and our carpet felt disgustingly sticky.
Reviewed on Aug 10, 2026
Nicollet Island Inn
Nicollet Island
$588
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Minneapolis (MSP)
9.2/10 Wonderful! (98 reviews)
If your looking to spend time in the room or dinning at the Nicollet Island Inn. I dont think you will be disappointed. Everything is close to the hotel. A quick Uber ride and your in down town Mpls or St.Paul. I have stayed here a few times. The thing I have liked is a simple thing. You get a real door key. Funny yes but not something one gets anymore.
Reviewed on Aug 5, 2026
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.
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.
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.
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.
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.
Osceola Hotel Deals
River Valley Inn & Suites
1030 N Cascade Street Osceola WI
Fully refundableReserve now, pay when you stay
$91 nightly
$101 total
Aug 16 - Aug 17
Total with taxes and fees
7.8/10 Good! (479 reviews)
"The property was close to my final destination. There was limited availability of personnel at the front desk."
Reviewed on Aug 11, 2026
Water Street Inn
101 Water St South Stillwater MN
Fully refundableReserve now, pay when you stay
$154 nightly
$173 total
Sep 7 - Sep 8
Total with taxes and fees
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 |
More vacations you might like
Frequently asked questions
How much does an Osceola vacation package cost?
Offering great value package deals from $306 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
- Hotels with Hot Tubs in Osceola
- Resorts & Hotels with Spas in St Croix Falls
- Cottages in Osceola
- Hotels with Hot Tubs in St Croix Falls
- Guest Houses in Dresser
- Motels in Dresser
- Pet-Friendly Hotels in St Croix Falls
- Americinn Hotels in St Croix Falls
- Osceola Hotels
- Hotels with a Pool in St Croix Falls
- Golf Hotels in St Croix Falls
- Somerset Hotels
- Amery Hotels
- Hotels with an Outdoor Pool in St Croix Falls
- Rv Parks in St Croix Falls
- Extended Stay Hotels in St Croix Falls
- Motels in Wanderoos
- Hudson Hotels
- Guest Houses in Osceola
- Hotels near Interstate State Park- Wisconsin
- Dresser Hotels
- Balsam Lake Hotels
- Hotels near Dancing Dragonfly Winery
- Hotels near St Croix National Scenic Riverway
- Hotels with an Indoor Pool in St Croix Falls
- Luxury Hotels in St Croix Falls
- St Croix Falls Hotels
- Hotels with Laundry Facilities in St Croix Falls
- Cabin Rentals in St Croix Falls
- 3 Star Hotels in Dresser
- Motels in St Croix Falls
- Cabin Rentals in Dresser
- Hotels near Osceola & St. Croix Valley Railway
- Cabin Rentals in Balsam Lake
- Pet-Friendly Hotels in Osceola
- Cabin Rentals in Osceola
- Aparthotels in Dresser
- Hotels near Fawn Doe Rosa Wildlife Educational Park
- New Richmond Hotels
- Family Hotels in Osceola
- Motels in Osceola
- Cottages in St Croix Falls
- Hotels with Bars in St Croix Falls
- Hotels near Trollhaugen
- Resorts & Hotels with Spas in Osceola
- Winery Hotels in St Croix Falls
- Vacation Homes in St Croix Falls
- 4 Star Hotels in Dresser
- B&B in St Croix Falls
- Cottage Winery and Vineyard
- Roberts Vacations
- Dancing Dragonfly Winery
- Where to stay in St Croix Falls
- Barron Vacations
- Great River Road Visitor & Learning Center
- The Dancing Bird
- River's Edge Apple River Campground
- St Croix National Scenic Riverway
- Turtle Lake Vacations
- Fawn Doe Rosa Wildlife Educational Park
- Siren Vacations
- Interstate State Park- Wisconsin
- Forts Folle Avoine Historical Park
- Visit Dresser
- St. Croix Casino Danbury
- New Richmond Heritage Center
- Apple River Hideaway
- River Falls Vacations
- Somerset Amphitheater
- Visit St Croix Falls
- Barron County Historical Society Pioneer Village Museum
- Balsam Lake Vacations
- Visit Osceola
- Luck Vacations
- St. Croix Casino Turtle Lake
- Crooked Lake Park
- St Croix Falls Vacations
- Wakanda Water Park
- Kinni Valley Riding Academy
- Osceola & St. Croix Valley Railway
- Willow River State Park
- Siren National Golf Club
- Luck Golf Course
- Car rental New Richmond
- Car rental Dresser
- Budget Rental Cars in St Croix Falls
- Standard Car Rentals in St Croix Falls
- Van Car Rentals in St Croix Falls
- Enterprise Rental Cars in Osceola
- Car rental St Croix Falls
- Enterprise Rental Cars in St Croix Falls
- Car rental Osceola
- Thrifty Car Rental Rental Cars in St Croix Falls
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
