Osceola County Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
Microtel Inn & Suites by Wyndham Sioux Falls

Microtel Inn & Suites by Wyndham Sioux Falls

2 out of 5
Mall District
Price was CA $965, price is now CA $925 per person
CA $925
per person
Dec 2 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Sioux Falls (FSD)
8/10 Very good! (136 reviews)
I loved the laminate floor, they always feel cleaner to me than carpet. Breakfast was fine. Our remote for the TV didn’t work, but the staff got right on it and replaced it. We were traveling with our dog and there was plenty of green space to walk him. That’s something I always appreciate when we’re traveling. Overall a good stay.

Reviewed on Oct 26, 2026

AeroStay Hotel

AeroStay Hotel

2.5 out of 5
North Sioux Falls
Price was CA $1,073, price is now CA $1,035 per person
CA $1,035
per person
Dec 2 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Sioux Falls (FSD)
9/10 Wonderful! (1,265 reviews)

My Place Hotel - Sioux Falls, SD

My Place Hotel - Sioux Falls, SD

2.5 out of 5
Mall District
Price was CA $976, price is now CA $942 per person
CA $942
per person
Dec 2 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Sioux Falls (FSD)
8.4/10 Very good! (1,000 reviews)

Valley Inn

Valley Inn

2.5 out of 5
University Heights
Price was CA $967, price is now CA $935 per person
CA $935
per person
Dec 2 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Sioux Falls (FSD)
8/10 Very good! (1,008 reviews)
The location is perfect if you have a loved one in the Sanford Hospital or if you have appts at Sanford. It is within walking distance. It is nothing fancy, but clean and beds were comfortable.

Reviewed on Oct 27, 2026

Hotel On Phillips

Hotel On Phillips

2.5 out of 5
Downtown Sioux Falls
Price was CA $1,104, price is now CA $1,078 per person
CA $1,078
per person
Dec 2 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Sioux Falls (FSD)
9.6/10 Exceptional! (1,622 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 $106 per night from Oct 30 to Oct 31
CA $106
CA $117 total
Oct 30 - Oct 31
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 $123 per night from Nov 27 to Nov 28
CA $123
CA $147 total
Nov 27 - Nov 28
includes taxes & fees
Lake Okoboji Resort & Conference Center
Reston Inn & Suites

Reston Inn & Suites

2.5 out of 5
10 11th Street S.E. Spencer IA
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Oct 30 to Oct 31
CA $113
CA $127 total
Oct 30 - Oct 31
includes taxes & fees
Reston Inn & Suites
See all 484 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Family Vacations

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 $925. 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.