Squirrel Hill South Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Squirrel Hill South
Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh
Downtown Pittsburgh
CA $1,143
per person
Nov 26 - Nov 29
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
8/10 Very good! (325 reviews)
Apartment was on a very busy street next to a 24 hr store and had a lot of people just standing around on the corner all day and night. Not the safest spot after dark. You could hear everything on the street all night, so hard to fall asleep. Building and hall smelled like weed but the apartment was fine. I texted the number that gave me the code and they said they would check the floor, address the issue and keep me posted. Never heard back from them. No thrills but didn’t expect any given the cost. Parking was supposed to be $25/day with in and out privileges in the assigned parking lot but there was never an attendant there so no in and out and charged $30/day.
Reviewed on Sep 20, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
CA $1,322
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Pittsburgh (PIT)
8.6/10 Excellent! (1,004 reviews)
I would highly recommend! We spent our 2nd anniversary there for the Steelers game and when we arrived to our room they were so kind to leave us some goodies and a little note to congratulate us! It was a very clean hotel and room! Staffing very kind! Will be staying again for sure!
Reviewed on Sep 14, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
CA $1,203
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Pittsburgh (PIT)
8.6/10 Excellent! (1,639 reviews)
Disappointed in the stay over considering it being a Hilton. Asked for towels for three days straight never got any. Front staff wasn’t exactly helpful.
Reviewed on Sep 22, 2026
Where to stay in Squirrel Hill South
Find the best Squirrel Hill South areas and neighborhoods for the activities you enjoy most. Learn more about Squirrel Hill South
Downtown Pittsburgh
2 out of top 10 points of interest in this area
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.
North Shore
2 out of top 10 points of interest in this area
Heinz Field, PNC Park, and The Andy Warhol Museum await in this vibrant area, connected to Downtown Pittsburgh by the iconic Roberto Clemente, Andy Warhol, and Rachel Carson Bridges. Enjoy easy access to two light rail stations.
Oakland
1 out of top 10 points of interest in this area
Academic and healthcare hub, Oakland boasts museums, shopping venues, and diverse dining options along Forbes and Fifth Avenue. Explore historic districts and easily navigate the area via the distinctive city steps and public transportation.
Strip District
Brimming with specialty shops, unique boutiques, and ethnic food purveyors, the Strip District offers a lively atmosphere with art studios, antique dealers, and the historic St. Stanislaus Kostka Church. Enjoy open-air markets and vibrant nightlife during summer months.
Shadyside
Victorian mansions and modern apartments create a diverse residential atmosphere. Explore upscale stores on Walnut Street, dine at local eateries like Pamela's Diner, and easily walk between the three business corridors. Public transportation is accessible.
Squirrel Hill South Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $173
CA $197 total
Oct 12 - Oct 13
includes taxes & fees
8.4/10 Very good! (3,819 reviews)
"Staff had good attitude and room was well kept."
Reviewed on Sep 22, 2026
Pittsburgh Marriott City Center
112 Washington Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $213
CA $243 total
Oct 22 - Oct 23
includes taxes & fees
8.2/10 Very good! (1,320 reviews)
"I have some specific feedback that I’d rather share with management directly."
Reviewed on Sep 21, 2026
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $169
CA $193 total
Oct 6 - Oct 7
includes taxes & fees
9.4/10 Exceptional! (2,350 reviews)
"No problems"
Reviewed on Sep 22, 2026
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.
Frequently asked questions
How much does a Squirrel Hill South vacation package cost?
Our Squirrel Hill South packages, which begin from just CA $1,143, are an awesome way to save loads of cash. Handpick your favorite hotels, flights and rental car to create a customized getaway.
How do I get a cheap travel package to Squirrel Hill South?
Browse and book everything in one place with our Squirrel Hill South vacation packages. You'll find deals on hotels, flights and more that'll keep your pocketbook happy and your adventurous side busy. And, with more than 550 air carriers and 1,000,000 hotel options worldwide to select from, there are endless opportunities to mix and match however you please.
Where should I stay in Squirrel Hill South?
Most travelers who visit Squirrel Hill South put both Acrisure Stadium and PNC Park on their itineraries. Why not consider a hotel right near these top attractions?
What are the top hotels in Squirrel Hill South?
Get your vacation off to a flying start by staying at Lovely, Cozy Beacon Guest Suite With Portable Kitchen In Squirrel Hill. It's one of most sought-after hotels in Squirrel Hill South. Another cozy option is Lovely, Cozy Murray Guest Suite In Squirrel Hill.
How far in advance should I book my Squirrel Hill South vacation?
It depends on the air carrier, but you can usually browse through international flights on Expedia nearly a year in advance. While it's generally a good idea to book ahead of time, lucky customers will sometimes score a cheaper flight only weeks before their intended journey.
What does an Expedia Squirrel Hill South travel package include?
It comes down to what kind of trip you have in mind. Squirrel Hill South vacation deals can include flights, car rentals and hotels. You can mix and match to create the bundle that suits you. You can also add on experiences and activities after you've booked to land even bigger discounts.
What should I know before booking a Squirrel Hill South travel package?
Whether it's adventure or relaxation you're after, a Squirrel Hill South vacation package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Squirrel Hill South Expedia vacation package?
Expedia has access to more than 550 airline partners worldwide, so you certainly can. Simply select the airline you want and craft your ideal Squirrel Hill South escape.
If I'm not able to travel, can I cancel my Squirrel Hill South vacation package?
It is possible to cancel your Squirrel Hill South booking if your plans have changed. Whether you'll be charged a fee 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 for more information.
Stay near popular Squirrel Hill South attractions
Schenley Park
Unwind with a walk along a wooded trail, or play a game of tennis or disc golf, in one of Pittsburgh’s largest and most popular parks.
Photo by Thomas Raia
Frick Park
Explore the great outdoors at Frick Park, a lovely green space in Pittsburgh. Attend a sporting event or visit the shops in this vibrant area.
Manor Theatre
6.0/10 (1 review)
You can get tickets for a performance at Manor Theatre during your trip to Pittsburgh. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
Things to do
Pittsburgh: Museum of Illusions Entrance Ticket
CA $40
per adult
94% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
CA $45
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
CA $18
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.