Osage Vacations from $678
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The Latest Osage vacation packages
Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Gillette
$685
per person
Sep 23 - Sep 30
found 8 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Gillette (GCC)
8/10 Very Good! (858 reviews)
Our first room had footprints on the bed sheets and extensive black mold on the ceiling. The front desk staff was helpful and switched us to a different room which did not have these problems. It's an older, dated facility, but once we got to a better room, it was comfortable to sleep. Breakfast was typical for a budget motel.
Reviewed on Aug 18, 2026
Osage Hotel Deals
Serena Inn & Suites - Sundance
2719 E Cleveland Street Sundance WY
Fully refundableReserve now, pay when you stay
$111 nightly
$125 total
Aug 21 - Aug 22
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
"Great hotel - clean and with super helpful staff that assisted us with our heavy cooler right up to our room. There is no elevator in the building, so it was much appreciated! They also switched us to a bit of a better room, which was a nice surprise as well. Breakfast was delicious and the room ..."
Reviewed on Aug 18, 2026
Arrowhead Motel
214 East Cleveland Street Sundance WY
$80 nightly
$90 total
Aug 19 - Aug 20
Total with taxes and fees
Newcastle Lodge and Convention Center
22918 US-85 Newcastle WY
Fully refundableReserve now, pay when you stay
$149 nightly
$167 total
Aug 19 - Aug 20
Total with taxes and fees
9/10 Wonderful! (583 reviews)
"The property is old"
Reviewed on Aug 17, 2026
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 Osage Vacation Packages
Osage Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
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Frequently asked questions
How much does an Osage vacation package cost?
You'll find cheap prices from $678 on Expedia for your Osage escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Osage costs.
What are the cheapest months to go to Osage?
You can usually find reduced prices and better availability in February, November and December. Browse our cheap Osage vacation packages and you could land some great off-season discounts.
How many days is enough for Osage?
With a well-organized itinerary, you can easily tick off the main Osage attractions in a few days. But if you'd like to explore off the beaten track or go on day tours, think about booking your Osage vacation for longer.
How to find the best Osage package deals?
Begin your search for an Osage package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Osage package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Osage escape underway.
Is it cheaper to book an Osage vacation as a package?
You can enjoy significant savings on your Osage getaway by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Osage?
Land incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Osage adventure.
Does Expedia offer Book Now, Pay Later Osage vacation packages?
Set off on your perfect escape to Osage with our Book Now, Pay Later vacations. There's no need to save up or hold off until your next payday — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stick to your budget and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
