Penn Vacations from $250

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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.
DoubleTree by Hilton Pittsburgh - Cranberry

DoubleTree by Hilton Pittsburgh - Cranberry

4 out of 5
Price was $335, price is now $250 per person
$250
per person
Jan 30 - Feb 2
found 14 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
8.8/10 Excellent! (913 reviews)
Besides the trash cans in lobby and outside needing emptied. Absolutely beautiful hotel. The lobby was gorgeous. Staff super friendly. Rooms were spotless!! 10 out of 10!!!

Reviewed on Nov 29, 2025

TownePlace Suites by Marriott Pittsburgh Cranberry Township

TownePlace Suites by Marriott Pittsburgh Cranberry Township

3 out of 5
Save 100% on your flight
Price was $567, price is now $320 per person
$320
per person
Jan 30 - Feb 2
found 14 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
9.2/10 Wonderful! (416 reviews)
The building is in good shape. One piece of furniture in our room was in poor shape but the rest of the room was fine and our stay was good. The breakfast is basic but sufficient.

Reviewed on Aug 17, 2025

The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
North Side
Price was $518, price is now $370 per person
$370
per person
Feb 15 - Feb 18
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,211 reviews)
So close to the stadium for the game, clean and friendly service

Reviewed on Dec 1, 2025

Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Price was $499, price is now $362 per person
$362
per person
Feb 15 - Feb 18
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,253 reviews)
Great hotel, excellent location.

Reviewed on Nov 25, 2025

Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was $383, price is now $280 per person
$280
per person
Feb 15 - Feb 18
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
8/10 Very Good! (1,003 reviews)
The room was very clean and the staff was extremely pleasant!

Reviewed on Dec 2, 2025

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Penn Hotel Deals

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue Pittsburgh PA
$104 nightly
The price is $119 total per night from Dec 21 to Dec 22
$119 total
Dec 21 - Dec 22
Total with taxes and fees
8.8/10 Excellent! (520 reviews)
Nice. Tv remote did not work, a fail there. They refused to reimburse for that. Fail. I adked for room service. They agreed but never showed up. Otherwise I loved the pool.

Reviewed on Nov 27, 2025

Courtyard by Marriott Pittsburgh University Center
Hampton Inn Pittsburgh/Monroeville

Hampton Inn Pittsburgh/Monroeville

2.5 out of 5
3000 Mosside Blvd Monroeville PA
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $109 total per night from Dec 14 to Dec 15
$109 total
Dec 14 - Dec 15
Total with taxes and fees
8/10 Very Good! (1,162 reviews)
Courteous Staff. Good breakfast. Free parking & WiFi

Reviewed on Nov 27, 2025

Hampton Inn Pittsburgh/Monroeville
Hyatt House Pittsburgh/Bloomfield/Shadyside

Hyatt House Pittsburgh/Bloomfield/Shadyside

3 out of 5
5335 Baum Blvd Pittsburgh PA
$142 nightly
The price is $162 total per night from Dec 17 to Dec 18
$162 total
Dec 17 - Dec 18
Total with taxes and fees
8.8/10 Excellent! (1,021 reviews)
Good location and convenient parking lot

Reviewed on Nov 26, 2025

Hyatt House Pittsburgh/Bloomfield/Shadyside
See all 685 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 $250 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.