Osceola Vacations from $308

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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.
Snelling Motel

Snelling Motel

2 out of 5
South Minneapolis
Price was $386, price is now $308 per person
$308
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Minneapolis (MSP)
7/10 Good! (172 reviews)
Room was clean but small. Only 1 chair (not very comfortable) in a room with a king-size bed makes it not very inviting in the daytime. Needs another chair. No hand soap at the sink. No hair dryer. No place to hang coats or other garments. Hard to find the spot to access hot water in the shower. Bed needed heavier blanket. About as basic as accommodations get. But the staff was friendly and helpful.

Reviewed on Dec 13, 2025

The Lofton Hotel, Tapestry Collection by Hilton

The Lofton Hotel, Tapestry Collection by Hilton

4.5 out of 5
Downtown Minneapolis
Save 100% on your flight
Price was $929, price is now $658 per person
$658
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Minneapolis (MSP)
9.4/10 Exceptional! (1,034 reviews)
Easy stay for baseball!

Reviewed on Jun 26, 2026

Emery, Autograph Collection Hotel

Emery, Autograph Collection Hotel

4.5 out of 5
Downtown Minneapolis
Price was $839, price is now $651 per person
$651
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Minneapolis (MSP)
9.2/10 Wonderful! (737 reviews)
The gym is clean and well stocked with equipment. Logan at the front desk was very helpful. Fantastic lobby.

Reviewed on Jun 6, 2026

Holiday Inn Express & Suites Eagan - Minneapolis Area by IHG

Holiday Inn Express & Suites Eagan - Minneapolis Area by IHG

2.5 out of 5
Price was $838, price is now $658 per person
$658
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Minneapolis (MSP)
9.2/10 Wonderful! (808 reviews)
The room was nice and we enjoyed the pool

Reviewed on Jun 22, 2026

Holiday Inn Express & Suites Bloomington - MPLS Arpt Area W by IHG

Holiday Inn Express & Suites Bloomington - MPLS Arpt Area W by IHG

3 out of 5
Price was $471, price is now $375 per person
$375
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Minneapolis (MSP)
8.6/10 Excellent! (1,003 reviews)
Room was clean but in rough shape, carpet was matted and deformed. Staff was excellent and the helpful with arranging shuttle.

Reviewed on Jun 6, 2026

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Stay near popular Osceola attractions

Osceola & St. Croix Valley Railway

8.6/5 (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.
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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
$95 nightly
The price is $105 total per night from Jun 28 to Jun 29
$105 total
Jun 28 - Jun 29
Total with taxes and fees
7.8/10 Good! (454 reviews)
"Call ahead if you cannot walk up the stairs etc as they don't have an elevator. It's 2 levels. The rooms we ok, a bit small, bathrooms pretty small. And hot tub jets were not working. Pool was pretty warm and it didn't smell overly like chlorine which was good."

Reviewed on Jun 22, 2026

River Valley Inn & Suites
MINNeSTAY* St. Croix Valley Inn

MINNeSTAY* St. Croix Valley Inn

Osceola WI
Get rates
MINNeSTAY* St. Croix Valley Inn
Water Street Inn

Water Street Inn

3.5 out of 5
101 Water St South Stillwater MN
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $177 total per night from Jun 28 to Jun 29
$177 total
Jun 28 - Jun 29
Total with taxes and fees
8.2/10 Very Good! (1,005 reviews)
"Excellent location and very attentive staff."

Reviewed on Jun 24, 2026

Water Street Inn
See all 469 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 $308 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.