Osceola County Vacation Packages

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Your Osceola County Vacation

With an Osceola County vacation package, you can forget about the hassle of planning and simply focus on experiencing what this interesting destination has to offer. Can't decide what should come first? Sibley is one of the most popular cities to explore during your trip to Osceola County. Expedia is a one-stop shop when it comes to organizing your Osceola County vacation. From accommodations and flights, to activities and rental cars, we're here to help you create a travel experience like no other.

Top Osceola County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Valley Inn

Valley Inn

2.5 out of 5
University Heights
Price was CA $1,424, price is now CA $1,370 per person
CA $1,370
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sioux Falls (FSD)
7.8/10 Good! (1,010 reviews)

Historic Twin Tudors Inn

Historic Twin Tudors Inn

3 out of 5
Price was CA $1,850, price is now CA $1,659 per person
CA $1,659
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sioux Falls (FSD)
8.8/10 Excellent! (3 reviews)
We were upgraded to staying at the Victorian Inn- i would highly recommended. The house is charming and located in the historic downtown of Sioux Falls.

Reviewed on Jun 16, 2025

La Quinta Inn & Suites by Wyndham Sioux Falls

La Quinta Inn & Suites by Wyndham Sioux Falls

3 out of 5
Mall District
Price was CA $1,501, price is now CA $1,439 per person
CA $1,439
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sioux Falls (FSD)
9.2/10 Wonderful! (1,509 reviews)
Overall, it was a good experience. The room was clean and spacious, and the staff were friendly and helpful. However, I needed to do some laundry; although there were laundry rooms on every floor, only one was actually working, so I had to wait for my turn and go to a different floor to do the wash. Aside from that, it was excellent.

Reviewed on Jul 24, 2026

AeroStay Hotel

AeroStay Hotel

2.5 out of 5
North Sioux Falls
Price was CA $1,539, price is now CA $1,479 per person
CA $1,479
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sioux Falls (FSD)
9/10 Wonderful! (1,175 reviews)

Hotel On Phillips

Hotel On Phillips

2.5 out of 5
Downtown Sioux Falls
Price was CA $1,734, price is now CA $1,673 per person
CA $1,673
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sioux Falls (FSD)
9.6/10 Exceptional! (1,492 reviews)

Osceola County Hotel Deals

Sibley Inn

Sibley Inn

2.5 out of 5
1108 2nd Avenue Sibley IA
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Jul 27 to Jul 28
CA $98
CA $108 total
Jul 27 - Jul 28
includes taxes & fees
Sibley Inn
Lake Okoboji Resort & Conference Center

Lake Okoboji Resort & Conference Center

3 out of 5
1405 Highway 71 Okoboji IA
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Aug 16 to Aug 17
CA $146
CA $175 total
Aug 16 - Aug 17
includes taxes & fees
7.8/10 Good! (1,006 reviews)
"Very nice outdoor pool. Very good breakfast bar."

Reviewed on Jul 24, 2026

Lake Okoboji Resort & Conference Center
Vintage Block Inn & Suites

Vintage Block Inn & Suites

2.5 out of 5
1107 Sanborn Ave Okoboji IA
The price is CA $170 per night from Aug 16 to Aug 17
CA $170
CA $193 total
Aug 16 - Aug 17
includes taxes & fees
9/10 Wonderful! (607 reviews)
"Loved it!"

Reviewed on Jul 24, 2026

Vintage Block Inn & Suites
See all 488 properties in Osceola County
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.
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Frequently asked questions

How much does an Osceola County vacation package cost?
Get ready to book, because a getaway to Osceola County starts from an affordable CA $1,370. When you combine your flights, hotels and car rentals into a travel package, you'll score the best bargains.
How do I get a cheap travel package to Osceola County?
Bundle your flights and hotels with Expedia to save on your next trip. With more than 550 partner airlines and 1,000,000 hotel options globally, your Osceola County vacation package can be customized exactly to suit your budget. With all those extra dollars, why not add one or more fun tours and activities? It's an easy way to unlock even more discounts. That vacation you've always dreamed of in Osceola County is much closer than you thought!
How far in advance should I book my Osceola County vacation?
Your best bet is to book early. Airlines generally release flights up to 12 months ahead of departure, and this is a fantastic opportunity to land some of the cheapest prices. Boss just told you to use up all your vacation days next week? No problem! Expedia are never short on fantastic bargains to help you have the getaway of your dreams, at an affordable price.
What does an Expedia Osceola County travel package include?
Expedia has all you need to arrange your Osceola County getaway, but how you structure your package depends on you. Choose from a combination of flights, hotels and rental cars. Looking for some activities or tours to fill in your time? Once you've made your booking, you can add them too. Whatever your budget or style, there's a package to meet your needs.
What should I know before booking an Osceola County travel package?
An Expedia travel package can be customized for your circumstances and is an easy way to make your money go further. What you include is completely up to you. Rental cars, hotels and flights — mix and match whatever combination suits your plans.
Can I choose my airline with an Osceola County Expedia vacation package?
Yes, you're in control. We have access to over 550 partner airlines all over the world, so you can tailor your Osceola County vacation according to your travel needs.
If I'm not able to travel, can I cancel my Osceola County vacation package?
You sure can, and we'll help you every step of the way. You may be able to change or cancel your Osceola County vacation package at no cost within 24 hours of booking. However, you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If life throws you a curveball, take a look at our Customer Service Portal for further information.

Stay near popular Osceola County attractions

Sibley Central Park

8.6/10 (14 reviews)
Explore the great outdoors at Sibley Central Park, a lovely green space in Sibley. Discover the area's entertainment venues and churches.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.