Penn Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.

Top Penn Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Americas Best Value Inn Pittsburgh Airport

Americas Best Value Inn Pittsburgh Airport

2 out of 5
Price was CA $1,231, price is now CA $1,118 per person
CA $1,118
per person
Dec 11 - Dec 14
found 14 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
6.6/10 (1,006 reviews)
Thanks.

Reviewed on Nov 3, 2026

Hilton Garden Inn Pittsburgh Airport

Hilton Garden Inn Pittsburgh Airport

3 out of 5
Price was CA $1,297, price is now CA $1,217 per person
CA $1,217
per person
Dec 11 - Dec 14
found 17 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
9/10 Wonderful! (1,003 reviews)
We liked that the room was clean. And the 24 hour shuttle was great. The staff was accommodating to our needs. And the Eat n Park next door was great for the kids.

Reviewed on Nov 4, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was CA $1,646, price is now CA $1,564 per person
CA $1,564
per person
Jan 8 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,697 reviews)

DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
Price was CA $1,674, price is now CA $1,595 per person
CA $1,595
per person
Jan 8 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.8/10 Excellent! (1,271 reviews)

Hyatt Regency Pittsburgh International Airport

Hyatt Regency Pittsburgh International Airport

3.5 out of 5
Price was CA $1,650, price is now CA $1,578 per person
CA $1,578
per person
Jan 8 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
9/10 Wonderful! (1,793 reviews)

Ready to book your vacation to Penn?

 

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Penn Hotel Deals

The Maverick by Kasa

The Maverick by Kasa

3 out of 5
120 S Whitfield St Pittsburgh PA
The price is CA $119 per night from Nov 9 to Nov 10
CA $119
CA $136 total
Nov 9 - Nov 10
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"Lovely place, convenient for going places and reasonable prices."

Reviewed on Nov 5, 2026

The Maverick by Kasa
Hyatt House Pittsburgh/Bloomfield/Shadyside

Hyatt House Pittsburgh/Bloomfield/Shadyside

3 out of 5
5335 Baum Blvd Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Nov 22 to Nov 23
CA $169
CA $193 total
Nov 22 - Nov 23
includes taxes & fees
Hyatt House Pittsburgh/Bloomfield/Shadyside
Comfort Inn & Suites Pittsburgh Fox Chapel

Comfort Inn & Suites Pittsburgh Fox Chapel

2.5 out of 5
180 Gamma Drive Pittsburgh PA
Fully refundable
The price is CA $116 per night from Nov 30 to Dec 1
CA $116
CA $133 total
Nov 30 - Dec 1
includes taxes & fees
Comfort Inn & Suites Pittsburgh Fox Chapel
See all 741 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Penn vacation package cost?
Offering great value package deals from CA $1,118 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.