Olean Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Olean

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
The price is S$179 per night from 1 Sept to 2 Sept
S$179
1 Sept - 2 Sept
includes taxes & fees
7/10 Good! (1,004 reviews)
Good Stay
"Good stay, the hotel is clean and the pool is fun, it's just all a little old feeling. The bartender at HK's was super fun and so accommodating."

Reviewed on 28 Jul, 2025

Lodge Of Four Seasons Golf Resort, Marina & Spa
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
The price is S$98 per night from 11 Aug to 12 Aug
S$98
11 Aug - 12 Aug
includes taxes & fees
6.8/10 (1,005 reviews)
"When we checked in and went to our room, we found that there wasn't a refrigerator in the room. My wife went to the desk and explained that we have meds that must be refrigerated. The gentleman at the front desk promptly brought one to us. Everything else was great from the start - it was clean and ..."

Reviewed on 30 Jul, 2025

Osage Village Inn
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
8/10 Very Good! (504 reviews)
"Great stay"

Reviewed on 2 Aug, 2025

Get rates
The Resort at Lake of the Ozarks
See all 1,863 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.

Frequently asked questions

How much does an Olean holiday package cost?
You can grab a holiday package to this popular destination on Expedia. However, how much your holiday 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?
January, February and November are great times to look for cheap Olean holiday packages. Opting to travel in quieter months means you can typically find better prices on accommodation and flights.
How many days is enough for Olean?
With a well-organised travel plan, you can easily hit the top Olean sights in a few days. But if you want to explore off the beaten track or go on day tours, think about booking your Olean holiday 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 holiday as a package?
An Expedia holiday 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 holiday 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.
How to plan a trip to Olean?

  1. Pick your travel dates: What you want to do in Olean and your favourite season can help you decide when to get away.
  2. Set your budget: Factor in costs such as flights, meals and transportation when working out how much to put aside for your trip to Olean. Then, pick a hotel that matches your budget, whether that's a wallet-friendly option or a more luxurious getaway.
  3. Work out your trip length: Think about how much time you want to spend exploring Olean. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your airfare and accommodation: After you've settled on your trip dates and duration, book the ideal Olean holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.