Shadyside 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 Shadyside
Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
CA $1,426
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Thunder Bay (YQT) to Pittsburgh (PIT)
8.4/10 Very good! (3,785 reviews)
We got an upgrade to a junior double suite from a double room which was great.
Staff was fantastic at check in & check out as well as restaurant. Very friendly!
Room was dated & not thoroughly cleaned.
We had to ask for soap.
We chose for the location which was perfect for attending a concert at Acrisure Stadium.
It was a 15 minute walk & a $10 golf cart ride.
Reviewed on Aug 31, 2026
Stay Pittsburgh
Downtown Pittsburgh
CA $1,464
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Thunder Bay (YQT) to Pittsburgh (PIT)
8/10 Very good! (321 reviews)
On the edge of downtown so area was a bit gritty. Bonus points: restaurants, museums, sport venues all within walking distance. Garage right across street is super convenient with in/out privileges, nice! Room I stayed in was a bit worn, but the price was right and the host very responsive.
Reviewed on Aug 30, 2026
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
CA $2,095
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Thunder Bay (YQT) to Pittsburgh (PIT)
8.6/10 Excellent! (222 reviews)
Perfect stay for the night! Clean, greeted by friendly staff, and convenient to all the downtown Pittsburgh things.
Reviewed on Aug 31, 2026
Where to stay in Shadyside
Find the best Shadyside areas and neighborhoods for the activities you enjoy most. Learn more about Shadyside
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.
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 Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $212
CA $242 total
Sep 15 - Sep 16
includes taxes & fees
8.4/10 Very good! (3,753 reviews)
"We got an upgrade to a junior double suite from a double room which was great. Staff was fantastic at check in & check out as well as restaurant. Very friendly! Room was dated & not thoroughly cleaned. We had to ask for soap. We chose for the location which was perfect for attending a concert at ..."
Reviewed on Aug 31, 2026
Omni William Penn Hotel
530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $291
CA $331 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (2,044 reviews)
"We are a family of 4, came for one night for a concert in town. Decided to splurge and stay at the Omni. What a wonderful experience. Old world glamour. Well maintained. Excellent hospitality- including "free drink" at any of their bars. Free Wifi Very comfortable beds (though full size), great size ..."
Reviewed on Aug 31, 2026
DoubleTree by Hilton Pittsburgh - Green Tree
500 Mansfield Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $135
CA $153 total
Sep 7 - Sep 8
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 Shadyside vacation package cost?
From just CA $1,426. Yes, you read that correctly. Our Shadyside vacation packages are the quickest way to make your dollars go much further. Combine your favorite hotels, flights and car rentals and explore this lively destination.
How do I get a cheap travel package to Shadyside?
Booking a Shadyside vacation package with Expedia is a great way to save. We have access to more than 550 partner airlines and 1,000,000 hotels across the globe. With such a broad range to pick from, you'll have no hassles creating your ideal escape.
Where should I stay in Shadyside?
Make sightseeing a breeze by staying someplace just a stone's throw away from Shadyside's biggest attractions. Acrisure Stadium and PNC Park are two traveler favorites.
What are the top hotels in Shadyside?
If it's your very first time in Shadyside, reserve a room at The Inn On Negley or Mansions on Fifth Hotel. Both hotels offer friendly service and are favorites among many savvy travelers.
How far in advance should I book my Shadyside vacation?
It can be tricky to know exactly when the best time is to book your Shadyside vacation. But typically the earlier you book, the better the prices. Sometimes, you can reserve your flights and hotels up to a year before departure. If you're eager to escape on a last-minute getaway, no need to worry! There are terrific bargains advertised on Expedia every day.
What does an Expedia Shadyside travel package include?
Flights, car rentals and hotels — we connect you to the best deals. All you'll have to do is pick and choose your favorite combination. After you've made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it easy to put together an unforgettable Shadyside trip.
What should I know before booking a Shadyside travel package?
You can save big by bundling your hotels, airfares and rental cars. Once you've made your booking, add on fun stuff like tours and activities. Your next awesome vacation is only a few clicks away.
Can I choose my airline with a Shadyside Expedia vacation package?
Yes, you're in charge. We offer more than 550 airlines worldwide, so you can tailor your Shadyside escape according to your travel preferences.
If I'm not able to travel, can I cancel my Shadyside vacation package?
We totally get that life can throw you the odd curveball. If you've booked a Shadyside vacation package and have to cancel or amend it, we can help. We suggest having a look at our Customer Service Portal first for information. But in general, if you've booked your package in the last 24 hours, you may be able to amend or cancel your itinerary at no cost. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.
Stay near popular Shadyside attractions
Walnut Street
During your trip to Pittsburgh, you can find the perfect gifts to bring home at Walnut Street. Savor the area's restaurants and bars.
Mellon Park Tennis Center
Catch an event at Mellon Park Tennis Center during your trip to Pittsburgh. Visit the area's shops, or simply enjoy its restaurants.
Gallerie CHIZ
You can spend an afternoon studying the exhibits at Gallerie CHIZ during your trip to Pittsburgh. Amble around this vibrant area's riverfront or experience its acclaimed theater scene.
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
CA $65
per adult
100% of travellers recommend
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.