Penn Vacations from $452
Book a Hotel + Flight or Car together to unlock savings
Your Penn Vacation
Organizing your next big getaway is a cinch with a Penn vacation package. The neighborhood of South Greensburg, which is great for dining, makes a good launchpad to discover the delights of this unique city. Make your trip to Penn even more fulfilling by going sightseeing. Seton Hill University, The Palace Theatre and Westmoreland Museum of American Art are some of the major attractions you'll want to explore. A couple of quick clicks is all it takes to put together the perfect Penn vacation on Expedia.
The Latest Penn vacation packages
Price found within the past 48 hours. Click for updated prices.
Villagio Boutique Hotel
North Side
$452
per person
Jan 2 - Jan 4
found 18 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
9.4/10 Exceptional! (164 reviews)
Easy check-in / check-out process.
Appreciate the free parking in the lot beside the hotel.
Large room (Alpine Suite) where we could relax in separate spaces
Reviewed on Oct 15, 2026
Stay Pittsburgh
Downtown Pittsburgh
$473
per person
Jan 2 - Jan 4
found 18 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
8/10 Very Good! (334 reviews)
Check in was rough online only. I couldn't reach anyone by phone, granted it was 10pm, but it took me forever to get through the process and then wait for a code to get into my room. Make sure you check in right when you get the text or email message.
Reviewed on Oct 17, 2026
Hilton Garden Inn Pittsburgh Airport
$628
per person
Dec 27 - Dec 31
found 2 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
9/10 Wonderful! (1,004 reviews)
I didn't like that I didn't get the exact room I ordered...I was advised that there is a glitch in system that allowed more rooms to be booked than availability i assume... The staff did what they could do which was ok the next day but it was just disappointing having to stay in a one bed room 1st night and then next day get moved to a two bed room the next day but I paid to have a two bed room suite which would've made my trip/experience a 5 star experience...
Reviewed on Oct 17, 2026
Penn Hotel Deals
The Maverick by Kasa
120 S Whitfield St Pittsburgh PA
$102 nightly
$117 total
Nov 16 - Nov 17
Total with taxes and fees
Hyatt House Pittsburgh/Bloomfield/Shadyside
5335 Baum Blvd Pittsburgh PA
Fully refundableReserve now, pay when you stay
$123 nightly
$140 total
Nov 18 - Nov 19
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Lovely hotel definitely will stay again"
Reviewed on Oct 18, 2026
Comfort Inn & Suites Pittsburgh Fox Chapel
180 Gamma Drive Pittsburgh PA
Fully refundable
$83 nightly
$95 total
Nov 8 - Nov 9
Total with taxes and fees
5.6/10 (1,007 reviews)
"It was fine. Like a lot of things in Pittsburgh it was a bit older than expected. Nothing particularly wrong or worth complaining about."
Reviewed on Oct 17, 2026
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 Penn Vacation Packages
Penn Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Arnold Palmer Regional Airport (LBE) |
Top Sights | Kennywood, The Palace Theatre and Boyce Park Ski Area |
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Frequently asked questions
How much does a Penn vacation package cost?
You'll find cheap prices from $452 on Expedia for your Penn escape. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Penn costs.
What are the cheapest months to go to Penn?
You can usually find lower rates and better availability in November, December and January. Explore our cheap Penn vacation packages and you could get some excellent off-season deals.
How many days is enough for Penn?
Usually, a handful of days is enough to see the main attractions during your Penn vacation. However, if you prefer to have some time to rest or go on day tours, think about extending your trip.
How to find the best Penn package deals?
Finding a cheap Penn package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most affordable Penn package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Penn vacation as a package?
An Expedia vacation package could land you great savings when compared to booking stays and flights individually. Better still, you can customize your Penn getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Penn?
If you have your Penn vacation dates confirmed, book as early as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for impromptu escapes.
Does Expedia offer Book Now, Pay Later Penn vacation packages?
Your Penn trip is meant to be an escape from your daily routine, not a reason for money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.