Penn Hills Holidays

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Your Penn Hills Holiday

The hassle-free way to experience this exciting city is with a customised Penn Hills holiday package. Stay in the neighbourhood 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 organising your perfect holiday to Penn Hills today.

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

Abundant dining options, interesting museums and live music are just a few top things to explore in Downtown Pittsburgh. A visit to PPG Paints Arena or Benedum Center might round out your trip, and you can jump aboard the metro at Wood Street Station or Steel Plaza Station to get around town.

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

Visitors often come to North Shore for its stunning river views, but many stay to explore sights like PNC Park and Acrisure Stadium. Getting around the area on the metro is easy if you take a ride at North Side Station.

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

Oakland is known for its ample dining options, and you can make a stop by Petersen Events Center and Carnegie Museum of Natural History while in the area.

Find hotels in Oakland
A bridge with illuminated lights reflecting on the water, a city skyline in the background, and a smokestack emitting smoke.

North Side

1 out of top 10 points of interest in this area

While you're in North Side, take in top sights like PNC Park or Acrisure Stadium, and hop on the metro to see more of the city at North Side Station or Allegheny Station.

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A courtyard with a fountain, brick walls, and trees.

Shadyside

Unique features of Shadyside include the restaurants and shopping. Make a stop by Walnut Street or Gallerie CHIZ while you're exploring the area.

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Top hotels in Penn Hills

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
£112
30 Aug - 31 Aug
includes taxes & fees
8.4/10 Very good! (3,715 reviews)
"Thought I left my phone in the room. Someone has escorted me back up after I checked out. I did end up finding it in my luggage and then the next day someone texted me to make sure that I have found it cause they had found a lost phone what a great group of individuals who work at this place the ..."

Reviewed on 26 Aug 2026

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
£87
7 Sept - 8 Sept
includes taxes & fees
The Landing Hotel at Rivers Casino
Omni William Penn Hotel

Omni William Penn Hotel

530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
£187
30 Aug - 31 Aug
includes taxes & fees
9.2/10 Wonderful! (2,063 reviews)
"The William Penn is an excellent hotel. The only problem during my stay was that the WiFi did not function properly for the first 36 hours. The hotel is beautiful. Highly recommend."

Reviewed on 25 Aug 2026

Omni William Penn Hotel
See all 2,010 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 Holidays
All Inclusive Holidays
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gay friendly holidays
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Frequently asked questions

How much does a Penn Hills travel package cost?
Starting from an incredible , you can tailor make your Penn Hills travel package. Simply bundle hotels, flights and car rentals and we'll reward you with discounts.
If I'm not able to travel, can I cancel my Penn Hills travel package?
It is possible to cancel your Penn Hills booking if your plans have been upended. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. It may be possible to change or cancel for free if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
How do I get a cheap travel package to Penn Hills?
Creating your own Penn Hills travel package with Expedia is a great way to save. We have more than 550 airlines and 1,000,000 properties throughout the world. With such a broad range to select from, you'll have no trouble pulling together your ideal trip.
Does Expedia offer Book Now, Pay Later Penn Hills holidays?
Good news! We do. Expedia has joined forces with online lender Klarna to help you easily pay for your holiday in instalments. Simply pick the payment plan that suits you best during the checkout process and take the stress out of budgeting for your trip. Be sure to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your holiday buck. Consider these flexible payment options below:
  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's monthly instalment plans. If making small repayments each month works for you, choose this option during the checkout process.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: Pressing the "book now" button is easier with this payment option. Simply put down a small deposit on your escape and then start working on your travel itinerary.
Where should I stay in Penn Hills?
A trip to Penn Hills wouldn't be complete without checking out Sri Venkateswara Temple, Monroeville Mall and Monroeville Convention Centre. Spend your nights near these tourist attractions and make sightseeing easy.
What are the top hotels in Penn Hills?
Get your escape off to a good start by booking a room at Hyatt Regency Pittsburgh International Airport. It's one of most popular properties in Penn Hills. Another comfortable option is Doubletree by Hilton Pittsburgh Greentree.
How far in advance should I book my Penn Hills holiday?
Get rewarded with the widest variety at the cheapest prices by booking your holiday to Penn Hills nice and early. Air carriers tend to advertise flight tickets anywhere up to a year before departure, so start locking things in as soon as possible. Having said that, Expedia is committed to providing you with the best bargains around, so it's never a bad time to book your dream holiday!
What does an Expedia Penn Hills travel package include?
Travel packages include hotels, rental cars and flights, but you can combine any of them to create your perfect Penn Hills trip. You can also add on fun things like tours and activities once you've made your booking. You're in the driver's seat! When you combine your bookings with Expedia, you'll score discounts you won't find anywhere else.
What should I know before booking a Penn Hills travel package?
When you book your flights, hotels and car rentals together, you'll walk away with great discounts. Whether you're organising a rural escape in a cottage or want to stay in a luxurious city hotel, Expedia can help make it happen.
Can I choose my airline with a Penn Hills Expedia travel package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the freedom to take your pick of available flights, hotels and activities that fit your needs.

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. Visit the shops and top-notch restaurants in this family-friendly area.
See properties

Things to do

Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

£36
per adult
100% of travellers recommend
Pittsburgh Pirates Baseball Game at PNC Park
Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

£22
per adult
90% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
Downtown Pittsburgh Hidden Gems Food Tour with 6 Food Tastings

Downtown Pittsburgh Hidden Gems Food Tour with 5 Food Tastings

£74
per adult
Downtown Pittsburgh Hidden Gems Food Tour with 5 Food Tastings
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. Flight-inclusive packages are ATOL protected.