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.
Hilton Garden Inn Pittsburgh Airport

Hilton Garden Inn Pittsburgh Airport

3 out of 5
Price was CA $878, price is now CA $679 per person
CA $679
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
9/10 Wonderful! (1,000 reviews)
Clean rooms, friendly staff

Reviewed on Sep. 1, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $2,189, price is now CA $1,472 per person
CA $1,472
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
7.6/10 Good! (20 reviews)
My room was very clean with a beautiful city view. The space is well thought out and very comfortable. There are also a lot of walkable shops and restaurants. Check-in was a little awkward as there was an event in front of the main entrance that I had to walk through with my luggage and speak very loudly over while checking in. Overall it was a nice getaway experience.

Reviewed on Sep. 2, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was CA $1,852, price is now CA $1,362 per person
CA $1,362
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.4/10 Very Good! (1,344 reviews)
Quick stay. Quiet rooms.

Reviewed on Sep. 3, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was CA $1,328, price is now CA $992 per person
CA $992
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.2/10 Very Good! (2,991 reviews)
The hotel was very nice. Rooms were a bit small but clean. There was a lot of road closures which made it hard to get to the entrance. Overall it was a nice stay and staff were amazing.

Reviewed on Sep. 6, 2025

Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
Price was CA $1,728, price is now CA $1,327 per person
CA $1,327
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,355 reviews)
This was an amazing property! Easy access off the highway. Walkable to all areas around.

Reviewed on Aug. 29, 2025

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
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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

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 $209 per night from Sep 28 to Sep 29
CA $209
CA $238 total
Sep 28 - Sep 29
includes taxes & fees
Wyndham Grand Pittsburgh Downtown
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
One Bigelow Square, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Sep 28 to Sep 29
CA $163
CA $186 total
Sep 28 - Sep 29
includes taxes & fees
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
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 $163 per night from Sep 21 to Sep 22
CA $163
CA $190 total
Sep 21 - Sep 22
includes taxes & fees
Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,719 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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Beach 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 $679, 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 which includes a city

PNC Park

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

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

Things to do

Visit beautiful shopping and dining complex in your private tour

Private City Kickstart Tour: Tokyo

CA $236
per adult
100% of travellers recommend
Private City Kickstart Tour: Tokyo
Pittsburgh Steelers Football Game at Acrisure Stadium

Pittsburgh Steelers Football Game at Acrisure Stadium

CA $38
per adult
Pittsburgh Steelers Football Game at Acrisure Stadium
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.