Penn Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Penn Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
CA $1,249
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Pittsburgh (PIT)
8.6/10 Excellent! (228 reviews)
The buildings architecture was awesome and in a good location to walk to the strip district, also took advantage of the free T train stop a short walk away. Room was very clean and spacious. It was basically a 1br apartment.
Would have liked a water cooler or something in the lobby.
Reviewed on Sep 19, 2026
Ready to book your vacation to Penn?
Penn Hotel Deals
Hyatt House Pittsburgh/Bloomfield/Shadyside
5335 Baum Blvd Pittsburgh PA
CA $201
CA $230 total
Oct 20 - Oct 21
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Great location, wonderful staff and very reasonable prices"
Reviewed on Sep 15, 2026
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
CA $217
CA $247 total
Oct 12 - Oct 13
includes taxes & fees
9/10 Wonderful! (935 reviews)
"Nice place"
Reviewed on Sep 19, 2026
Hilton Garden Inn Pittsburgh University Place
3454 Forbes Ave Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $201
CA $229 total
Oct 18 - Oct 19
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Comfy beds, close to hospital, coffee and tea bar available. Would have preferred a la carte breakfast. I would not pay 17.00buffet price for toast and apple."
Reviewed on Sep 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.
Frequently asked questions
How much does a Penn vacation package cost?
Offering great value package deals from CA $633 on Expedia, you'll be pleasantly surprised at how much a vacation to Penn costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Penn?
You can typically find lower rates and greater availability in January, February and March. Check out our cheap Penn vacation packages and you could score some great off-season deals.
How many days is enough for Penn?
We'd suggest booking a Penn vacation for a minimum of 2 days. This will allow you enough time to visit major attractions including Westmoreland Museum of American Art and Big Mac Museum, as well as check out neighbourhoods like South Greensburg and Southwest Greensburg. You could even squeeze in a day trip beyond Penn.
How to find the best Penn package deals?
Use Expedia's filters to help you find some unbeatable Penn package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Penn package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Penn vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still get the freedom to create a tailored Penn vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Penn?
If you're planning a spontaneous Penn adventure, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Penn?
- Choose when to get away: Check your schedule and get packing. Your preferred time of year and the available activities will also help you decide when to vacation in Penn.
- Work out your budget: Make sure you have enough money to pay for everything from transportation and meals to airfares and activities. Your hotel will likely be the largest expense during your trip to Penn.
- Set the duration of your trip: Start by compiling a list of the sights and activities you want to experience in Penn. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick a Penn vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
