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 Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,847, price is now CA $1,488 per person
CA $1,488
per person
Apr 10 - Apr 13
just found
Roundtrip non-stop flight included
Montreal (YMQ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay.

Reviewed on Jan 10, 2026

Melwood Suites Unit 107 Studio

Melwood Suites Unit 107 Studio

2 out of 5
Oakland
Price was CA $5,027, price is now CA $4,156 per person
CA $4,156
per person
Apr 22 - Apr 25
found 5 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Pittsburgh (PIT)
9.6/10 Exceptional! (41 reviews)
The studio itself was very nice! The only annoying thing was the outside door pin pad takes multiple tries. The room facing the street was kind of noisy in the evenings.

Reviewed on Dec 2, 2025

City Sights 2 Queen Beds Downtown Apt

City Sights 2 Queen Beds Downtown Apt

2 out of 5
Downtown Pittsburgh
Price was CA $4,272, price is now CA $3,547 per person
CA $3,547
per person
Apr 22 - Apr 25
found 16 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Pittsburgh (PIT)
6/10 (1 review)
Downtown 1 Bedroom Apt Clean Safe Walkable

Downtown 1 Bedroom Apt Clean Safe Walkable

2 out of 5
Downtown Pittsburgh
Price was CA $3,279, price is now CA $2,741 per person
CA $2,741
per person
Apr 22 - Apr 25
found 16 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Pittsburgh (PIT)
No reviews

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 which includes a bridge and a river or creek

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 $158 per night from Mar 22 to Mar 23
CA $158
CA $180 total
Mar 22 - Mar 23
includes taxes & fees
8.2/10 Very Good! (3,438 reviews)
Very quiet room, convenient location

Reviewed on Mar 9, 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 $216 per night from Mar 21 to Mar 22
CA $216
CA $247 total
Mar 21 - Mar 22
includes taxes & fees
9.2/10 Wonderful! (1,967 reviews)
Convenient all around

Reviewed on Mar 9, 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 $136 per night from Mar 16 to Mar 17
CA $136
CA $158 total
Mar 16 - Mar 17
includes taxes & fees
8.4/10 Very Good! (1,475 reviews)
Ideal location

Reviewed on Mar 9, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,939 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
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Family Vacations

Frequently asked questions

How much does a Squirrel Hill vacation package cost?
Our Squirrel Hill vacation packages, which begin from just CA $1,488, 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

The Gates Hillman Center is a unique building that houses the computer science program and research. I love how outside the box the building is #StunningStructures

Carnegie Mellon University

4.5/5(21 reviews)

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 which includes a city

PNC Park

4.5/5(67 reviews)

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

PNC Park
Mario Lemieux statue

PPG Paints Arena

5/5(80 reviews)

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

Looking up to find cool details in the Downtown Skyline

Best of the Burgh Walking Tour of Pittsburgh

CA $45
per adult
100% of travellers recommend
Best of the Burgh Walking Tour of Pittsburgh
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
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
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.