Squirrel Hill South Vacation Packages
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Top Holiday Package Deals in Squirrel Hill South
Price found within the past 48 hours. Click for updated prices.
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
CA $1,620
per person
Sep 25 - Sep 28
found 12 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,000 reviews)
The staff at the Westin was extremely helpful and proactive. The initial room they gave us had some issues, including a smoke-like smell (not cigarette smoke). As soon as we notified reception, someone handled it extremely professionally, and within minutes we were moved to a much better room.
Reviewed on Aug 3, 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.
North Side
1 out of top 10 points of interest in this area
If you're spending time in North Side, check out sights like PNC Park or Acrisure Stadium and hop on the metro to see more the city at North Side Station or Allegheny Station.
Mount Washington
Consider a visit to Ohio River Valley and take some time to enjoy the abundant dining options during your time in Mount Washington. If you want to see more of the city, jump on the metro at South Hills Junction Station or Palm Garden Station.
Squirrel Hill South Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $173
CA $198 total
Sep 1 - Sep 2
includes taxes & fees
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $167
CA $190 total
Aug 23 - Aug 24
includes taxes & fees
9.4/10 Exceptional! (2,118 reviews)
"The hotel was very modern. The room was sorta clean, very dusty everywhere. Hair was also all around. The staff was very helpful, the breakfast was delicious and the valet parking was the icing on the cake! I truely enjoyed my time spent at the landing hotel!"
Reviewed on Aug 6, 2026
Omni William Penn Hotel
530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $251
CA $286 total
Aug 9 - Aug 10
includes taxes & fees
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 $767, 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 family-friendly 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 acclaimed theater scene in this vibrant area.
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
CA $73
per adult
100% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
CA $41
per adult
90% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
CA $46
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.