Penn Hills 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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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.
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

Downtown Pittsburgh
CA $1,358
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.2/10 Very good! (1,320 reviews)
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh
Save 100% on your flight
CA $1,935
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,000 reviews)
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh
CA $1,525
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,659 reviews)
Stay Pittsburgh

Stay Pittsburgh

Downtown Pittsburgh
CA $1,360
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Pittsburgh (PIT)
8/10 Very good! (332 reviews)
Etage Executive Living

Etage Executive Living

Downtown Pittsburgh
CA $1,808
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,909 reviews)
Etage inside is great. The rooms and rooftop are fabulous. The bus stop right outside and the homeless gathered round it and around the corner are not.The politicians in all these great cities Suck!

Reviewed on Oct 3, 2026

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
A yellow bridge over a river with a cityscape in the background.

Downtown Pittsburgh

2 out of top 10 points of interest in this area

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
A yellow bridge over a river, a weeping willow tree, and a modern building with glass windows.

North Shore

2 out of top 10 points of interest in this area

Heinz Field, PNC Park, and The Andy Warhol Museum await in this vibrant area, connected to Downtown Pittsburgh by the iconic Roberto Clemente, Andy Warhol, and Rachel Carson Bridges. Enjoy easy access to two light rail stations.

Find hotels in North Shore
The Mellon Institute at Carnegie Mellon University with classical columns and a Gothic cathedral in the background.

Oakland

1 out of top 10 points of interest in this area

Academic and healthcare hub, Oakland boasts museums, shopping venues, and diverse dining options along Forbes and Fifth Avenue. Explore historic districts and easily navigate the area via the distinctive city steps and public transportation.

Find hotels in Oakland
A street with a Starbucks and a plaza with colorful steps.

Strip District

Brimming with specialty shops, unique boutiques, and ethnic food purveyors, the Strip District offers a lively atmosphere with art studios, antique dealers, and the historic St. Stanislaus Kostka Church. Enjoy open-air markets and vibrant nightlife during summer months.

Find hotels in Strip District
A courtyard with a fountain, brick walls, and trees.

Shadyside

Victorian mansions and modern apartments create a diverse residential atmosphere. Explore upscale stores on Walnut Street, dine at local eateries like Pamela's Diner, and easily walk between the three business corridors. Public transportation is accessible.

Find hotels in Shadyside

Penn Hills Hotel Deals

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $176
CA $201 total
Oct 22 - Oct 23
includes taxes & fees
Wyndham Grand Pittsburgh Downtown
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $186
CA $212 total
Nov 3 - Nov 4
includes taxes & fees
9.4/10 Exceptional! (2,388 reviews)
"Excellent place to stay"

Reviewed on Oct 3, 2026

The Landing Hotel at Rivers Casino
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

500 Mansfield Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $148
CA $169 total
Nov 3 - Nov 4
includes taxes & fees
DoubleTree by Hilton Pittsburgh - Green Tree
See all 2,000 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
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

Frequently asked questions

How much does a Penn Hills vacation package cost?
From as low as CA $1,358. 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.

Stay near popular Penn Hills attractions

Sri Venkateswara Temple

8.8/10 (187 reviews)
After visiting Sri Venkateswara Temple, make a plan to see the other sights and activities in Pittsburgh. Check out the shops and top-notch restaurants in this family-friendly area.
See properties

Things to do

Picture 4 for Activity Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

CA $41
per adult
86% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
This tour is the best tour for sports fans! Big fun guaranteed!

Black & Gold Pittsburgh History Tour for Sports Fans

CA $45
per adult
Black & Gold Pittsburgh History Tour for Sports Fans
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

CA $18
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
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.