Penn Vacations from $473

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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.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $759, price is now $473 per person
$473
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (3,506 reviews)
Room was run down/old. Shower head was coming out of the wall and couldnt get the water hot. The phone in the room was making a loud buzzing noise so I just disconnected the cord. Rest of venue and area was super.l, staff was friendly. Room was clean. Easy access.to a late.checkout that was needed.

Reviewed on May 6, 2026

City Sights 2 Queen Beds Downtown Apt

City Sights 2 Queen Beds Downtown Apt

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,076, price is now $870 per person
$870
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
6/10 (1 review)
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $714, price is now $579 per person
$579
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip flight included
New York (LGA) to Pittsburgh (PIT)
8/10 Very Good! (272 reviews)
Once you book the room trough expedia there is a list of communication in order to get the access to the property.. This should be advised once received expedia confirmation in order to expedite the process

Reviewed on May 7, 2026

2 Bedroom 2 Bath City Views

2 Bedroom 2 Bath City Views

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,018, price is now $826 per person
$826
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
No reviews
2 Bedroom Downtown Apt City Views Park Walk

2 Bedroom Downtown Apt City Views Park Walk

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $997, price is now $809 per person
$809
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
2/10 (1 review)
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Penn Hotel Deals

Hilton Garden Inn Pittsburgh University Place

Hilton Garden Inn Pittsburgh University Place

3 out of 5
3454 Forbes Ave Pittsburgh PA
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $147 total per night from May 27 to May 28
$147 total
May 27 - May 28
Total with taxes and fees
8.8/10 Excellent! (1,021 reviews)
We had a wonderful time! The location is super convenient, just a short walk to Pittsburgh University and a quick drive to CMU. The only thing that could have been better was that the elevator key card access wasn’t working when we were there, which was a bit of a safety concern for the guests.

Reviewed on May 8, 2026

Hilton Garden Inn Pittsburgh University Place
Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $148 total per night from May 25 to May 26
$148 total
May 25 - May 26
Total with taxes and fees
9/10 Wonderful! (709 reviews)
I checked in late and exhausted. The staff member that checked me in was super friendly and kind. He asked my preference for floor and near or away from the elevator. The location of this hotel is very convenient for visiting my children at Pitt and CMU.

Reviewed on May 7, 2026

Courtyard by Marriott Pittsburgh University Center
The Maverick by Kasa

The Maverick by Kasa

3 out of 5
120 S Whitfield St Pittsburgh PA
$114 nightly
The price is $130 total per night from May 21 to May 22
$130 total
May 21 - May 22
Total with taxes and fees
9/10 Wonderful! (959 reviews)
Beautiful and unique

Reviewed on May 8, 2026

The Maverick by Kasa
See all 749 properties in Penn
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 $473 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.