Olean Vacations from $334

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The Latest Olean vacation packages

Price found within the past 48 hours. Click for updated prices.
Finns Motel

Finns Motel

2.5 out of 5
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Columbia (COU)
8/10 Very Good! (314 reviews)
All around was a good place to stop and cheap

Reviewed on Aug 6, 2025

Greenlight Inn & Suites

Greenlight Inn & Suites

2 out of 5
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Columbia (COU)
8.6/10 Excellent! (309 reviews)
Bathroom door warped could not close without lifting the door. Furniture was stained & old. Breakfast was a not hot,tasteless & limited. We would not stay there again. Staff was pleasant, but the place is old and needs to be renovated. Also there are very few places in the area.

Reviewed on Aug 7, 2025

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Olean Hotel Deals

Lodge Of Four Seasons Golf Resort, Marina & Spa

Lodge Of Four Seasons Golf Resort, Marina & Spa

4 out of 5
315 Four Seasons Dr., Lake Ozark, MO
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $132 total per night from Sep 7 to Sep 8
$132 total
Sep 7 - Sep 8
Total includes taxes and fees
7/10 Good! (1,001 reviews)
Weekend getaway
"The hotel is clean, but definitely dated. Fun quarky things about it :) we enjoyed our stay. The bed was super comfy. We only were able to see 2 restaurants open… the HK one was not our favorite, it was pricey and frozen food :/ The food we had at the pool (nachos) were pretty good. HUGE portion ..."

Reviewed on Aug 4, 2025

Lodge Of Four Seasons Golf Resort, Marina & Spa
Capitol Plaza Hotel Jefferson City

Capitol Plaza Hotel Jefferson City

3.5 out of 5
Jefferson City 415 W. McCarty St, Jefferson City, MO
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Sep 1 to Sep 2
$107 total
Sep 1 - Sep 2
Total includes taxes and fees
6.8/10 (1,000 reviews)
"Wonderful"

Reviewed on Aug 3, 2025

Capitol Plaza Hotel Jefferson City
Osage Village Inn

Osage Village Inn

2.5 out of 5
4616 Osage Beach Parkway, Osage Beach, MO
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $77 total per night from Aug 31 to Sep 1
$77 total
Aug 31 - Sep 1
Total includes taxes and fees
6.8/10 (1,000 reviews)
"Accommodations were fine for the price. Continental breakfast not till 7:30, little late for working folks"

Reviewed on Aug 5, 2025

Osage Village Inn
See all 1,859 properties in Olean
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 Olean vacation package cost?
You can grab a vacation package to this popular destination from $334 on Expedia. However, how much your vacation to Olean costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Olean?
You can typically find lower rates and better availability in November, December and January. Browse our cheap Olean vacation packages and you could get some great off-season deals.
How many days is enough for Olean?
With a well-planned itinerary, you can easily hit the top Olean sights in a handful of days. But if you want to explore off the beaten track or take day trips, think about booking your Olean vacation for longer.
How to find the best Olean package deals?
Begin your search for an Olean package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Olean package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Olean escape off to a flying start.
Is it cheaper to book an Olean vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels separately. Better still, you can tailor your Olean trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Olean?
Enjoy incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Olean trip.
Does Expedia offer Book Now, Pay Later Olean vacation packages?
If you're anything like us, you love discovering new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Olean vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.