Penn Hills Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

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

    Plan, book, and manage your trip all in one place

Your Penn Hills Vacation

The hassle-free way to experience this exciting city is with a customized Penn Hills vacation package. Stay in the neighborhood of Squirrel Hill South, which is great for cycling, golfing and dining or choose someplace else — our package deals are all about you. If taking in sights is on the agenda during your trip to Penn Hills, stop by major attractions like Carnegie Mellon University, Kennywood and Pittsburgh Zoo and PPG Aquarium. Check out Expedia's extensive range of travel options and start organizing your perfect vacation to Penn Hills today.

Top Holiday Package Deals in Penn Hills

Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
per person
Sep 19 - Sep 22
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
7.6/10 Good! (142 reviews)
Clean and quiet property in downtown Pittsburgh. Had some difficulty leaving the Allied garage because my QR code or the scanner wasn’t working, but otherwise a great stay. Will definitely stay again if I’m in the area.

Reviewed on Jul. 6, 2025

Renaissance Pittsburgh Hotel

Renaissance Pittsburgh Hotel

4 out of 5
Downtown Pittsburgh
per person
Sep 19 - Sep 22
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
9/10 Wonderful! (1,002 reviews)
Absolutely loved the hotel. The room was very spacious and had a fantastic view. The staff was great. The bar inside the hotel was relaxed and the bartender was awesome. There is so many dining options within walking distance from the hotel. During my stay they was doing the Picklesburgh Festival, and this did not impact my stay at all. It was a great stay, planning to do it again soon.

Reviewed on Jul. 11, 2025

TRYP by Wyndham Pittsburgh/Lawrenceville

TRYP by Wyndham Pittsburgh/Lawrenceville

3 out of 5
Lawrenceville
per person
Sep 19 - Sep 22
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
8.6/10 Excellent! (819 reviews)
The room was not very clean

Reviewed on Jul. 7, 2025

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Downtown Pittsburgh
per person
Sep 19 - Sep 22
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
8.2/10 Very Good! (1,003 reviews)
Staff was great!! A+

Reviewed on Jul. 1, 2025

The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
North Side
per person
Sep 19 - Sep 22
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
9.4/10 Exceptional! (803 reviews)
Did not like parking and having to walk far

Reviewed on Jul. 10, 2025

Where to stay in Penn Hills

Find the best Penn Hills areas and neighborhoods for the activities you enjoy most. Learn more about Penn Hills
Downtown Pittsburgh which includes a bridge and a river or creek

Downtown Pittsburgh

2 out of top 10 points of interest in this area
4.5/5(187 area reviews)

Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.

Find hotels in Downtown Pittsburgh

Penn Hills Hotel Deals

Wyndham Grand Pittsburgh Downtown
Wyndham Grand Pittsburgh Downtown
3.5 out of 5
600 Commonwealth Pl, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Jul 16 to Jul 17
CA $170
CA $194 total
Jul 16 - Jul 17
includes taxes & fees
8/10 Very Good! (2,881 reviews)
"The hotel was nice and clean and a short walking distance to the park and baseball stadium."

Reviewed on Jul. 8, 2025

Wyndham Grand Pittsburgh Downtown
Omni William Penn Hotel
Omni William Penn Hotel
4 out of 5
530 William Penn Place, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from Jul 27 to Jul 28
CA $196
CA $224 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (1,530 reviews)
"It was a very cool experience staying at this historic hotel. It's in a great area. The lobby is stunning. The room we stayed in was spacious but nothing fancy. Our bed was very uncomfortable - it caved into the middle. The friendly staff gave offered us a breakfast credit for the bad sleep. Overall ..."

Reviewed on Jul. 9, 2025

Omni William Penn Hotel
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Joinery Hotel Pittsburgh, Curio Collection by Hilton
4 out of 5
453 Boulevard of the Allies, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Jul 16 to Jul 17
CA $173
CA $198 total
Jul 16 - Jul 17
includes taxes & fees
8.2/10 Very Good! (1,323 reviews)
"Friendly and clean"

Reviewed on Jul. 10, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,837 properties in Penn Hills
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 Hills vacation package cost?
From as low as CA $807. Yes, you read that right. Our Penn Hills vacation packages are the quickest way to make your dollar go further. Combine your preferred flights, hotels and rental car and explore this vibrant destination.
How do I get a cheap travel package to Penn Hills?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and rental cars --- we've got everything you need. Pick the combination that suits you and see your savings grow. We know a package deal is never one-size-fits-all. That's why we offer over 550 air carriers and 1,000,000 properties worldwide, which lets you customize your Penn Hills adventure.
Where should I stay in Penn Hills?
A getaway to Penn Hills isn't complete without visiting Sri Venkateswara Temple, Monroeville Convention Center and Monroeville Mall. Spend your nights close to these top sights and make sightseeing easy.
How far in advance should I book my Penn Hills vacation?
It depends on the airline, but it's usually possible to compare international airfares on Expedia up to 12 months in advance. While it's generally recommended to book ahead of time, lucky travelers will sometimes score a cheaper flight just weeks before their intended journey.
What does an Expedia Penn Hills travel package include?
Choose from a combination of hotels, flights and rental cars. Once you've made your booking, you can add experiences and tours. Want to pick your fare class? That's also possible. The choice is yours when it comes to organizing your dream Penn Hills escape.
What should I know before booking a Penn Hills travel package?
Our prices are always low. However, you'll snap up even more savings if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll always get transparent pricing and loads of choice.
Can I choose my airline with a Penn Hills Expedia vacation package?
Yes --- that's the beauty of an Expedia vacation package. You get to choose. We have access to more than 550 airline partners all over the world, so you have lots of choice when organizing your Penn Hills trip.
If I'm not able to travel, can I cancel my Penn Hills vacation package?
Yes, it's possible to cancel your Penn Hills booking if your plans have been upended. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Penn Hills

PNC Park which includes a city

PNC Park

4.5/5(67 reviews)

Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.

PNC Park
University of Pittsburgh

University of Pittsburgh

4.5/5(36 reviews)

Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

University of Pittsburgh
Carnegie Mellon University

Carnegie Mellon University

4.5/5(21 reviews)

Walk around the campus of Carnegie Mellon University, a top college in Pittsburgh. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Carnegie Mellon University

Things to do

Visit beautiful shopping and dining complex in your private tour

Private City Kickstart Tour: Tokyo

CA $185
per adult
100% of travellers recommend
Private City Kickstart Tour: Tokyo
JUST THE TOUR - An open top Double Decker Bus Sightseeing Tour of Pittsburgh.

JUST THE TOUR - Double Decker bus sightseeing tour of Pittsburgh.

CA $62
per adult
94% of travellers recommend
JUST THE TOUR - Double Decker bus sightseeing tour of Pittsburgh.
Happy hour cruiser

2 Hour Private Sightseeing Charter Boat Cruise

CA $529
per traveller
2 Hour Private Sightseeing Charter Boat Cruise
See all activities in Pittsburgh
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.