Olean Vacations from $427

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The Latest Olean vacation packages

Price found within the past 48 hours. Click for updated prices.
Greenlight Inn & Suites

Greenlight Inn & Suites

2 out of 5
Price was $451, price is now $427 per person
$427
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Columbia (COU)
8.6/10 Excellent! (413 reviews)
The room was clean. Staff was friendly. Breakfast was good but wish they had more juices to choose from. Would have been nice if coffee and tea bar was open at all times.

Reviewed on Jan 19, 2026

Treehouse LOZ Seclusion for 6!

Treehouse LOZ Seclusion for 6!

4 out of 5
Shawnee Bend
Price was $1,305, price is now $1,201 per person
$1,201
per person
May 18 - May 24
found 17 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Columbia (COU)
No reviews
Finns Motel

Finns Motel

2.5 out of 5
Price was $457, price is now $432 per person
$432
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Columbia (COU)
8/10 Very Good! (330 reviews)
Found this awesome (older) hotel. Very comfortable & enjoyed our night stay. Bathroom very small - but again older, very well maintained hotel.

Reviewed on Oct 16, 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
$128 nightly
The price is $140 total per night from Mar 29 to Mar 30
$140 total
Mar 29 - Mar 30
Total with taxes and fees
7.4/10 Good! (1,102 reviews)
The shower knob was lose so kind of a pain when showered and the bed was not comfortable unfortunately so I did not sleep. And there is no complimentary coffee besides what’s in the room. Other than that, the staff was great , the firep

Reviewed on Feb 24, 2026

Lodge Of Four Seasons Golf Resort, Marina & Spa
DoubleTree by Hilton Hotel Jefferson City

DoubleTree by Hilton Hotel Jefferson City

4 out of 5
422 Monroe St Jefferson City MO
$118 nightly
The price is $136 total per night from Mar 8 to Mar 9
$136 total
Mar 8 - Mar 9
Total with taxes and fees
8.4/10 Very Good! (723 reviews)
This is one of the best examples of a successful hotel “makeover” I have ever experienced. My last stay there (before the remodel) was less than satisfactory. This Doubletree Hilton property today is just amazing! Everything from the cleanliness, the staff, the amenities, every aspect is just a wonderful ...

Reviewed on Feb 15, 2026

DoubleTree by Hilton Hotel Jefferson City
The Resort at Lake of the Ozarks

The Resort at Lake of the Ozarks

3 out of 5
3080 Bagnell Dam Blvd Lake Ozark MO
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $115 total per night from Mar 3 to Mar 4
$115 total
Mar 3 - Mar 4
Total with taxes and fees
8/10 Very Good! (570 reviews)
Yes

Reviewed on Feb 8, 2026

The Resort at Lake of the Ozarks
See all 1,930 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.

Find the Best Olean Vacation Packages

Olean Essential Information

Language
English
Currency
U.S dollars

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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 $427 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.