Osceola Holidays

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Osceola Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Minneapolis/Bloomington

Hilton Minneapolis/Bloomington

4 out of 5
West Bloomington
Price was S$2,527, price is now S$2,170 per person
S$2,170
per person
4 Sept - 11 Sept
found 1 day ago
Return flight included
Singapore (SIN) to Minneapolis (MSP)
9.2/10 Wonderful! (1,007 reviews)
Great customer service and the loved the cleanliness of everything.

Reviewed on 13 Jul, 2026

The Lofton Hotel, Tapestry Collection by Hilton

The Lofton Hotel, Tapestry Collection by Hilton

4.5 out of 5
Downtown Minneapolis
Price was S$2,628, price is now S$2,230 per person
S$2,230
per person
4 Sept - 11 Sept
found 1 day ago
Return flight included
Singapore (SIN) to Minneapolis (MSP)
9.4/10 Exceptional! (1,048 reviews)
Location is excellent. Hotel is immaculate. Staff is over the top friendly. The rooms are priced really reasonable.

Reviewed on 12 Jul, 2026

Graduate by Hilton Minneapolis

Graduate by Hilton Minneapolis

4 out of 5
Dinkytown
Price was S$2,717, price is now S$2,335 per person
S$2,335
per person
4 Sept - 11 Sept
found 1 day ago
Return flight included
Singapore (SIN) to Minneapolis (MSP)
9.2/10 Wonderful! (1,060 reviews)
Close meaning in the heart of the U of MN and surrounded by the stadiums. with access to the light rail and bus directly in front of the hotel.

Reviewed on 10 Jul, 2026

Mystic Lake Casino Hotel

Mystic Lake Casino Hotel

3.5 out of 5
Price was S$2,603, price is now S$2,244 per person
S$2,244
per person
4 Sept - 11 Sept
found 1 day ago
Return flight included
Singapore (SIN) to Minneapolis (MSP)
9/10 Wonderful! (2,611 reviews)
Stayed during the craziness of the Jack Johnson concert but the staff were efficient and extremely kind and helpful. They definitely handled the influx of a large crowd smoothly and maintained top notch customer service. It was also very clean and comfortable. We thoroughly enjoyed our stay!

Reviewed on 14 Jul, 2026

Top hotels in Osceola

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
The price is S$139 per night from 16 Jul to 17 Jul
S$139
16 Jul - 17 Jul
includes taxes & fees
7.8/10 Good! (463 reviews)
"Overpriced. Continental breakfast is bagels cereal and a waffle machine. No hot food other than make your own waffles. No dresser for clothes, phone in room did not work so no way to contact desk. No elevator."

Reviewed on 12 Jul, 2026

River Valley Inn & Suites
Water Street Inn

Water Street Inn

3.5 out of 5
101 Water St South Stillwater MN
Fully refundableReserve now, pay when you stay
The price is S$252 per night from 19 Jul to 20 Jul
S$252
19 Jul - 20 Jul
includes taxes & fees
8.2/10 Very good! (1,017 reviews)
"Loved our stay but need to update historic charm with better lighting and room darkening shades."

Reviewed on 13 Jul, 2026

Water Street Inn
Hudson Inn & Suites

Hudson Inn & Suites

3 out of 5
811 Dominion Drive Hudson WI
Fully refundableReserve now, pay when you stay
The price is S$124 per night from 27 Jul to 28 Jul
S$124
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (862 reviews)
"Someone else said old but well maintained. They were correct. I walked into the room and the AC was off. It was about 80 in the room. No odd smell. Just hot. The AC cooled it down quickly and efficiently. The sheets were soft. Choice of flat or fat pillows. Bed was hard, but at least it was clean ..."

Reviewed on 14 Jul, 2026

Hudson Inn & Suites
See all 482 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.

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. Autumn excursions showcase spectacular foliage while you experience the charm of historic rail travel.
See properties

Frequently asked questions

How much does an Osceola holiday package cost?
Offering great value package deals from S$2,170 on Expedia, you'll be thrilled with how little a holiday to Osceola costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Osceola?
October, November and December are great times to search for cheap Osceola holiday packages. Opting to travel in quieter months means you can generally find lower prices on flights and hotels.
How many days is enough for Osceola?
With a well-organised schedule, you can easily tick off the most popular Osceola sights in a handful of days. But if you want to venture off the beaten track or take day trips, think about booking your Osceola holiday for longer.
Is it worth booking a holiday package to Osceola?
It's easy to see why an Osceola holiday is on the to-do list of many travellers. Popular attractions like Osceola & St. Croix Valley Railway are just the beginning of what you can explore here.
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 holiday package as soon as possible.
Is it cheaper to book an Osceola holiday as a package?
Expedia holiday 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 personalised Osceola holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Osceola?
If you have your Osceola holiday 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.
How to plan a trip to Osceola?

  1. Pick your travel dates: What you plan to do in Osceola and your favourite season can help you decide when to get away.
  2. Budget wisely: Besides the cost of your stay, you'll need to consider other expenses. These include flights, food and transportation. Also, set aside a little extra for unexpected costs that may arise during your trip to Osceola.
  3. Set the duration of your trip: Start by making a list of all the attractions you want to get to in Osceola. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find an Osceola holiday package that brings all your bookings together.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.