Squirrel Hill Vacation Packages

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Top Holiday Package Deals in Squirrel Hill

Price found within the past 48 hours. Click for updated prices.
The Colonial Mt. Lebanon by Luxe PGH

The Colonial Mt. Lebanon by Luxe PGH

3 out of 5
Mount Lebanon
Price was CA $1,261, price is now CA $1,026 per person
CA $1,026
per person
Jun 5 - Jun 7
found 21 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
2/10 (2 reviews)
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $2,356, price is now CA $1,716 per person
CA $1,716
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.4/10 Very Good! (81 reviews)
The bed was very comfortable, the kitchen was great, the TV was nice but no local channels, I didn't use the washer/dryer but nice to have in the room. The only issue was road noise came through the large windows.

Reviewed on Mar 31, 2026

Hilton Garden Inn Pittsburgh University Place

Hilton Garden Inn Pittsburgh University Place

3 out of 5
Central Oakland
Price was CA $1,484, price is now CA $1,177 per person
CA $1,177
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.8/10 Excellent! (1,006 reviews)
Loved the location just that it was a LOUD hotel. Not sure if we were next to the service elevator but heard bangs, opening closing of doors all night!

Reviewed on Apr 6, 2026

Hilton Garden Inn Uniontown

Hilton Garden Inn Uniontown

3 out of 5
Price was CA $1,799, price is now CA $1,445 per person
CA $1,445
per person
May 14 - May 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
9/10 Wonderful! (629 reviews)
Clean room, friendly staff and wonderful lobby with areas to gather with friends and family around an indoor or outdoor fire.

Reviewed on Apr 5, 2026

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

2.5 out of 5
North Shore
Price was CA $1,913, price is now CA $1,551 per person
CA $1,551
per person
May 15 - May 18
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,398 reviews)
Room was clean and comfortable. Front desk was friendly and helpful with any questions. Breakfast area could have been kept cleaner. Convenient property for PNC park! Would stay again.

Reviewed on Apr 5, 2026

Where to stay in Squirrel Hill

Find the best Squirrel Hill areas and neighborhoods for the activities you enjoy most. Learn more about Squirrel Hill
Downtown Pittsburgh

Downtown Pittsburgh

2 out of top 10 points of interest in this area
4.5/5(190 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

Squirrel Hill 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 $193 per night from Apr 21 to Apr 22
CA $193
CA $220 total
Apr 21 - Apr 22
includes taxes & fees
8.2/10 Very Good! (3,456 reviews)
Valet guys were great. Great hustle! Rooms were dated but location was perfect

Reviewed on Apr 7, 2026

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 $243 per night from Apr 30 to May 1
CA $243
CA $277 total
Apr 30 - May 1
includes taxes & fees
9.2/10 Wonderful! (1,983 reviews)
Absolutely gorgeous hotel. Incredibly clean and quiet, and all around amazing. My only complaint is that the "bouncer" for the speakeasy was rude. He at one point told the lady next to me that we needed to "calm down" because we were laughing. It was saint Patrick's day weekend and the other guests ...

Reviewed on Apr 6, 2026

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 $215 per night from Apr 12 to Apr 13
CA $215
CA $250 total
Apr 12 - Apr 13
includes taxes & fees
8.4/10 Very Good! (1,479 reviews)
We’ve stayed here many times. Always great

Reviewed on Apr 4, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 2,003 properties in Squirrel Hill
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
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Frequently asked questions

How much does a Squirrel Hill vacation package cost?
Our Squirrel Hill vacation packages, which begin from just CA $1,026, are the easiest way to save big. Pick and choose your favorite flights, hotels and rental cars to create your perfect escape.
How do I get a cheap travel package to Squirrel Hill?
Browse and lock in everything in the one place with our Squirrel Hill vacation packages. We have incredible bargains on flights, hotels, tours and more that'll keep your credit card happy and your adventurous spirit busy. And, with more than 550 partner airlines and 1,000,000 hotel options around the globe to select from, you'll have endless opportunities to mix and match as you want.
Where should I stay in Squirrel Hill?
Most who travel to Squirrel Hill include Acrisure Stadium and PNC Park on their to-do lists. Why not go for a hotel as close as possible to these great attractions?
What are the top hotels in Squirrel Hill?
If it's your first time staying in Squirrel Hill, make a reservation at The Mansion At Maple Heights or Pittsburgh Townhome ~ 5 Miles To Market Square. Both hotels offer friendly service and are favorites among many travelers.
How far in advance should I book my Squirrel Hill vacation?
Smart travelers will likely want to reserve their seats as early as possible. You can generally look up international fares on Expedia up to 12 months before your flight. If you're booking at the last minute, there's no need to worry. Budget prices occasionally become available just weeks before departure dates.
What does an Expedia Squirrel Hill travel package include?
That depends on you. You can select from a range of Squirrel Hill bundles, such as a hotel, rental car and flight. You can also book a flight and a hotel, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your dream Squirrel Hill escape looks like, you're sure to save!
What should I know before booking a Squirrel Hill travel package?
Discover deals that match your budget with an Expedia package. Flights, hotels, rental cars — we've got them all. You'll save loads just by combining your bookings. Whether you're taking off on a ski trip or sipping cocktails on a beach, your dream getaway is just clicks away.
Can I choose my airline with a Squirrel Hill Expedia vacation package?
Yes, so take your pick! We offer more than 550 partner airlines throughout the world, so you can design your Squirrel Hill adventure according to your budget and travel needs.
If I'm not able to travel, can I cancel my Squirrel Hill vacation package?
Whether it's your hotel or flight, you can cancel or alter it. Booked your Squirrel Hill vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings made more than 24 hours ago, you may incur a fee from your airline, hotel or car rental company. For more information, browse our Customer Service Portal. We'll help you every step of the way.

Discover the most popular places to visit in Squirrel Hill

Carnegie Mellon University

Carnegie Mellon University

Take a campus tour or just explore the area of Carnegie Mellon University, during your trip to Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

Carnegie Mellon University
PNC Park

PNC Park

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

PNC Park
PPG Paints Arena

PPG Paints Arena

Catch an event at PPG Paints Arena during your trip to Pittsburgh. Experience the acclaimed theater scene or attend a sporting event in this vibrant area.

PPG Paints Arena

Things to do

Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

CA $40
per adult
80% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
Make new friends as you learn the exciting history of whiskey in Pittsburgh

Whiskey Rebellion & Prohibition Tour

CA $67
per adult
Whiskey Rebellion & Prohibition Tour
Pittsburgh: Beauty of the Burgh Bike Tour

Pittsburgh: Beauty of the Burgh Bike Tour

CA $81
per adult
94% of travellers recommend
Pittsburgh: Beauty of the Burgh Bike Tour
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.