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.
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
CA $1,700
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Pittsburgh (PIT)
8.6/10 Excellent! (1,639 reviews)
Checking in took over 2 hours because rooms were ready.
Reviewed on Sep 24, 2026
Traveler's Rest Hotel
South Side Flats
CA $1,588
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Pittsburgh (PIT)
9.6/10 Exceptional! (118 reviews)
Very clean, owners were very nice and friendly, great place to stay, especially if you are going to watch the Steelers!
Reviewed on Sep 18, 2026
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
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 Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $174
CA $199 total
Oct 12 - Oct 13
includes taxes & fees
8.4/10 Very good! (3,785 reviews)
"The room we stayed in was older and not very bright. It was clean but which we would have had a renovated room. Housekeeping was amazing and very nice."
Reviewed on Sep 24, 2026
Pittsburgh Marriott City Center
112 Washington Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $215
CA $245 total
Oct 16 - Oct 17
includes taxes & fees
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $189
CA $216 total
Oct 18 - Oct 19
includes taxes & fees
9.4/10 Exceptional! (2,359 reviews)
"Wonderful stay!! I love everything about this hotel I stay here at least twice a month or more !"
Reviewed on Sep 24, 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 vacation package cost?
Our Squirrel Hill vacation packages, which begin from just CA $1,530, 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.
Stay near popular Squirrel Hill attractions
Temple Sinai
Temple Sinai is just one of the places to see in Pittsburgh, so why not enjoy the other things to explore during your travels? Experience the acclaimed theater scene or attend a sporting event in this vibrant area.
Pittsburgh Center for the Arts
Enjoy an outing to Pittsburgh Center for the Arts during your stay in Pittsburgh. Stroll along the riverfront or attend a sporting event in this vibrant area.
Purnell Center for the Arts
Enjoy an outing to Purnell Center for the Arts during your stay in Pittsburgh. Make some time to visit the shops while you're in the area.
Hunt Institute for Botanical Documentation
You can spend an afternoon studying the exhibits at Hunt Institute for Botanical Documentation in Pittsburgh. Amble around this family-friendly area's riverfront or attend a sporting event.
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
CA $54
per adult
100% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
CA $41
per adult
86% of travellers recommend
Whiskey Rebellion & Prohibition Tour
CA $69
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.