Squirrel Hill Vacation Packages

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

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The Latest Squirrel Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Reception
    Aug 16 - Aug 19

    Americas Best Value Inn Pittsburgh Airport + Flight

    Coraopolis
    3 nights
    2.0 star property
    6.6/10 - (1,010 reviews)
    "The room wasn’t clean. The carpet was VISIBLY DIRTY, no swept at all. There was still trash left in the bathroom from previous guest. The previous guests left their shampoo and stuff inside the shower, was never cleaned out. The entire room smelled like complete cigarettes and it’s supposed to be a “”smoke free” room. There were other guests knocking on our door all throughout the night asking for water, cigarettes, rides to the store. The sheets were stained badly and the lady who checked me..."
    Reviewed June 9, 2026
    Roundtrip • Montreal (YUL) - Pittsburgh (PIT)
    YUL - PIT • Nonstop PIT - YUL • Nonstop
    CA $1,028
    CA $910
    per traveller
    found 10 hours ago
    Americas Best Value Inn Pittsburgh Airport
  • Front of property
    Aug 16 - Aug 19

    Stay Pittsburgh + Flight

    Downtown Pittsburgh
    3 nights
    2.0 star property
    8.0/10 - Very good (293 reviews)
    "Had an entire apartment for 1 person. Had everything necessary and highly recommend. Great communication."
    Reviewed June 8, 2026
    Roundtrip • Montreal (YUL) - Pittsburgh (PIT)
    YUL - PIT • Nonstop PIT - YUL • Nonstop
    CA $1,161
    CA $971
    per traveller
    found 10 hours ago
    Stay Pittsburgh
  • Exterior
    Aug 16 - Aug 19

    The Westin Pittsburgh, a Marriott Hotel + Flight

    Downtown Pittsburgh
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,000 reviews)
    Roundtrip • Montreal (YUL) - Pittsburgh (PIT)
    YUL - PIT • Nonstop PIT - YUL • Nonstop
    CA $1,517
    CA $1,306
    per traveller
    found 10 hours ago
    The Westin Pittsburgh, a Marriott Hotel
  • Terrace/patio
    Aug 16 - Aug 19

    Joinery Hotel Pittsburgh, Curio Collection by Hilton + Flight

    Downtown Pittsburgh
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,534 reviews)
    "Super decorative, cozy, and the rooms were super clean! Valet was quick and convenient!"
    Reviewed June 8, 2026
    Roundtrip • Montreal (YUL) - Pittsburgh (PIT)
    YUL - PIT • Nonstop PIT - YUL • Nonstop
    CA $1,097
    CA $954
    per traveller
    found 10 hours ago
    Joinery Hotel Pittsburgh, Curio Collection by Hilton
  • Indoor pool
    Aug 14 - Aug 16

    DoubleTree by Hilton Pittsburgh - Green Tree + Flight

    Pittsburgh
    2 nights
    4.0 star property
    8.6/10 - Excellent (1,014 reviews)
    "Great!"
    Reviewed June 10, 2026
    Roundtrip • Montreal (YUL) - Pittsburgh (PIT)
    YUL - PIT • Nonstop PIT - YUL • Nonstop
    CA $1,437
    CA $1,272
    per traveller
    found 8 hours ago
    DoubleTree by Hilton Pittsburgh - Green Tree

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 $208 per night from Jul 9 to Jul 10
CA $208
CA $237 total
Jul 9 - Jul 10
includes taxes & fees
8.2/10 Very Good! (3,618 reviews)
"Clean and great location"

Reviewed on Jun 10, 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 $264 per night from Jun 14 to Jun 15
CA $264
CA $301 total
Jun 14 - Jun 15
includes taxes & fees
9.2/10 Wonderful! (2,026 reviews)
"Old tired hotel with friendly staff."

Reviewed on Jun 9, 2026

Omni William Penn Hotel
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Jun 14 to Jun 15
CA $200
CA $228 total
Jun 14 - Jun 15
includes taxes & fees
9.4/10 Exceptional! (1,804 reviews)
"It was a very easy, problem-free experience. I would recommend staying again definitely."

Reviewed on Jun 9, 2026

The Landing Hotel at Rivers Casino
See all 2,025 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Squirrel Hill vacation package cost?
Our Squirrel Hill vacation packages, which begin from just , 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

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
PNC Park

PNC Park

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

PNC Park
Acrisure Stadium

Acrisure Stadium

Giant ketchup bottles tilt onto the scoreboard to celebrate touchdowns in this innovative riverside football arena at the heart of Pittsburgh sports.

Acrisure Stadium

Things to do

Picture 4 for Activity 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
This tour is the best tour for sports fans! Big fun guaranteed!

New! Black & Gold Sports History Tour for Sports Fans

CA $45
per adult
New! Black & Gold Sports 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.