Olean Vacations from $510

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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.
Regency Retreat

Regency Retreat

3 out of 5
Price was $628, price is now $510 per person
$510
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Buffalo (BUF)
10/10 Exceptional! (2 reviews)
house was clean and neat

Reviewed on Nov 1, 2026

The Eagles Nest, Couples Escape - Hot Tub & Views

The Eagles Nest, Couples Escape - Hot Tub & Views

4.5 out of 5
Price was $3,489, price is now $2,332 per person
$2,332
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Buffalo (BUF)
9.2/10 Wonderful! (7 reviews)
We had a wonderful weekend stay at this house! Clean, comfortable, and had everything we needed for a relaxing getaway. The location was perfect—peacefully tucked near the mountains while still being just 5 minutes from town, making it easy to enjoy both nature and local shops and restaurants.

Reviewed on Aug 4, 2026

The Allen House

The Allen House

3.5 out of 5
Price was $2,680, price is now $1,817 per person
$1,817
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Buffalo (BUF)
No reviews

Summer Street Guest House

Summer Street Guest House

3 out of 5
Bryant
Price was $1,155, price is now $838 per person
$838
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Buffalo (BUF)
9.6/10 Exceptional! (4 reviews)
Loved the house, the owner, and his dog!

Reviewed on Jul 2, 2026

The Lincoln Boutique Motel

The Lincoln Boutique Motel

2 out of 5
Price was $2,024, price is now $1,535 per person
$1,535
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Buffalo (BUF)
9.8/10 Exceptional! (97 reviews)

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Stay near popular Olean attractions

Gargoyle Park

7.8/10 (22 reviews)
Gargoyle Park offers Olean's first disc golf course alongside scenic Allegheny River Valley Trail access. Enjoy outdoor recreation or reserve the pavilion with gas stoves for family gatherings and summer festivals.
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Olean Hotel Deals

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
$92 nightly
The price is $104 total per night from Dec 3 to Dec 4
$104 total
Dec 3 - Dec 4
Total with taxes and fees
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
$99 nightly
The price is $112 total per night from Nov 26 to Nov 27
$112 total
Nov 26 - Nov 27
Total with taxes and fees
Best Western Plus University Inn
Fairfield Inn & Suites by Marriott Olean

Fairfield Inn & Suites by Marriott Olean

3 out of 5
3270 Route 417 Olean NY
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $151 total per night from Nov 8 to Nov 9
$151 total
Nov 8 - Nov 9
Total with taxes and fees
9/10 Wonderful! (489 reviews)
"The staff and cleanliness were above the expectation!!"

Reviewed on Nov 3, 2026

Fairfield Inn & Suites by Marriott Olean
See all 609 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

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Frequently asked questions

What's included in an Olean vacation package?
An Olean vacation package lets you combine round-trip flights, a hotel stay, and a rental car, offering convenience for exploring this ski destination outside the city. Many hotels here offer free breakfast, providing a good start to your day without extra planning. The primary airport serving the area is Buffalo Niagara International Airport (BUF).

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a Olean vacation package?
When you bundle, you can save up to 30%*. To save money on a Olean package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's the best vacation package for Olean?
For a romantic Olean vacation package, consider a stay at Fairfield Inn & Suites by Marriott Olean, rated 9 out of 10. This hotel offers an indoor pool and travelers often highlight its spacious facilities, making it a comfortable base for couples.

Families looking for the best vacation packages in Olean might prefer Hampton Inn & Suites Olean, rated 8.7 out of 10. It features an indoor pool and is pet friendly, with travelers frequently noting the relaxing facilities.

If you're seeking a budget-friendly Olean vacation package, Microtel Inn & Suites by Wyndham Olean/Allegany, rated 8.3 out of 10, is a solid choice. It includes free breakfast and is pet friendly, with travelers praising its newly remodeled rooms. Another option is Best Western Plus University Inn, rated 8 out of 10, which also offers free breakfast and an indoor pool, and is noted for its nice-sized rooms.
What are the top things to do in Olean?
Olean, a ski destination outside the city, offers a mix of outdoor adventures and scenic views for your Olean vacation:

Browse and book things to do in Olean on Expedia.
Do you need to rent a car in Olean, or is public transport enough?
For an Olean vacation package, a rental car offers the most flexibility, especially since it's a ski destination outside the city. While the city's core, including the Union-State St downtown area, is walkable enough to get around, many attractions and outdoor activities are spread out. The Olean Area Transit System (OATS) provides local public transit with 6 routes serving Olean and the surrounding area. However, for exploring the wider region or reaching ski areas, a car is highly recommended. The nearest major airport, Buffalo Niagara International Airport (BUF), is about 60 miles away, making a car convenient for arrival and departure with your Olean vacation packages with flights.
Are Olean vacation package hotels conveniently located?
Olean vacation package hotels offer convenient access to the central area and nearby attractions. Many hotels are situated close to central Olean, making it easy to explore the city. For example, Hampton Inn & Suites Olean is about 1 mile from central Olean, while Holiday Inn Express Olean by IHG is about a 10-minute walk away. Further out, Fairfield Inn & Suites by Marriott Olean is about 2 miles from central Olean. Choosing a hotel in or near central Olean for your Olean vacation package provides easy access to local sights and dining.
Can I change or cancel my Olean vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Olean vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Olean vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Olean vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Olean?
To find last-minute vacation packages to Olean, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Olean vacation packages?
Free cancellation on a Olean vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Olean vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Olean getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Olean vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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