Olean Vacations from $406

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Your Olean Vacation

Choose a Olean vacation package and you can focus on what matters — having some fun. This means no more stressful planning, just more time to experience the best parts of this awesome city, such as its lush beauty and rich history. St. Bonaventure University, Rock City Park and Cutco-Ka-Bar Visitors Center are just some of the sights you'll want to see during your trip to Olean. Don't delay your visit to this city any longer. Your ultimate Olean vacation is just a few clicks away with Expedia.

The Latest Olean vacation packages

Price found within the past 48 hours. Click for updated prices.
Old Library Inn Olean NY

Old Library Inn Olean NY

2 out of 5
Price was $580, price is now $406 per person
$406
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Buffalo (BUF)
9.2/10 Wonderful! (35 reviews)
Best staff!!! Lois is the most wonderful person and we absolutely love her!!!

Reviewed on May 2, 2026

The Allen House

The Allen House

3.5 out of 5
Save 100% on your flight
Price was $1,199, price is now $792 per person
$792
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Buffalo (BUF)
No reviews
Buffalo Airport Hotel

Buffalo Airport Hotel

3 out of 5
Save 100% on your flight
Price was $665, price is now $442 per person
$442
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Buffalo (BUF)
8/10 Very Good! (3,005 reviews)
Really nice hotel for the price. Comfortable beds. Close to the airport. Close to restaurants.

Reviewed on May 21, 2026

The Richardson Hotel

The Richardson Hotel

3.5 out of 5
Elmwood Bidwell
Save 100% on your flight
Price was $1,002, price is now $756 per person
$756
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Buffalo (BUF)
9/10 Wonderful! (1,012 reviews)
The historical building was fantastic and its location is very convenient to showing, restaurants, attractions, and lovely neighborhoods. Would definitely stay here again!

Reviewed on May 22, 2026

Curtiss Hotel, an Ascend Collection Hotel

Curtiss Hotel, an Ascend Collection Hotel

5 out of 5
Downtown Buffalo
Save 100% on your flight
Price was $1,227, price is now $932 per person
$932
per person
Aug 1 - Aug 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Buffalo (BUF)
9.4/10 Exceptional! (1,000 reviews)
We loved the hot spring pool!

Reviewed on May 14, 2026

Don't see what you're looking for?
See all available trips from Pretty Prairie to Olean
View all trips

Discover the most popular places to visit in Olean

sculpture of a lion

Gargoyle Park

Explore the great outdoors at Gargoyle Park, a lovely green space in Olean. Visit the area's shops, or simply enjoy its restaurants.

Gargoyle Park

Cutco-Ka-Bar Visitors Center

After visiting Cutco-Ka-Bar Visitors Center, make a plan to see the other sights and activities in Olean. While in this family-friendly area, you can enjoy the restaurants.

Cutco-Ka-Bar Visitors Center

Olean Hotel Deals

Holiday Inn Express Olean by IHG

Holiday Inn Express Olean by IHG

2.5 out of 5
101 Main St Olean NY
Fully refundable
$116 nightly
The price is $137 total per night from Jun 1 to Jun 2
$137 total
Jun 1 - Jun 2
Total with taxes and fees
8.8/10 Excellent! (752 reviews)
"The breakfast was delightful and the staff who served it was incredibly friendly."

Reviewed on May 19, 2026

Holiday Inn Express Olean by IHG
Microtel Inn & Suites by Wyndham Olean/Allegany

Microtel Inn & Suites by Wyndham Olean/Allegany

2 out of 5
3234 Nys Route 417 Olean NY
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $121 total per night from Jun 7 to Jun 8
$121 total
Jun 7 - Jun 8
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
"Place was nice"

Reviewed on May 22, 2026

Microtel Inn & Suites by Wyndham Olean/Allegany
Best Western Plus University Inn

Best Western Plus University Inn

2.5 out of 5
3051 W State Street Olean Olean NY
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $125 total per night from May 31 to Jun 1
$125 total
May 31 - Jun 1
Total with taxes and fees
8.8/10 Excellent! (853 reviews)
"The bed was so comfortable. The staff friendly and helpful!"

Reviewed on May 3, 2026

Best Western Plus University Inn
See all 588 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
Closest Airport
Bradford Regional Airport (BFD)
Population
13,900
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
St. Bonaventure University, Rock City Park and Gargoyle Park

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Olean vacation package cost?
Offering great value package deals from $406 on Expedia, you'll be thrilled with how little a vacation to Olean costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Olean?
July, November and December are the best times to look for cheap Olean vacation packages. Traveling in quieter periods means you can generally find reduced prices on hotels and flights.
How many days is enough for Olean?
Generally, a handful of days is enough to go to the major attractions during your Olean vacation. But if you'd like to have more time to kick back or take day trips, consider extending your itinerary.
How to find the best Olean package deals?
Use Expedia's handy filters to find some terrific Olean package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Olean package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book an Olean vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging stays and flights individually. Better still, you can customize your Olean escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Olean?
If you have your Olean vacation dates confirmed, book early to grab some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Olean vacation packages?
If you're like us, you love going away but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Olean trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.