Shadyside Vacation Packages

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Top Holiday Package Deals in Shadyside

Price found within the past 48 hours. Click for updated prices.
Homewood Suites by Hilton Pittsburgh Southpointe

Homewood Suites by Hilton Pittsburgh Southpointe

3 out of 5
Price was CA $1,254, price is now CA $987 per person
CA $987
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Pittsburgh (PIT)
8.8/10 Excellent! (1,001 reviews)
Service was great. Property needs updated, mostly the bathrooms. Cheap materials, all the showeres are gross, gross appearance as if no one cleans them...despite me going to purchase cleaning solutions it still appeared to be dirty.

Reviewed on Aug. 24, 2025

Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was CA $2,170, price is now CA $1,340 per person
CA $1,340
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Pittsburgh (PIT)
8.2/10 Very Good! (1,006 reviews)
Changed rooms 3 times as TV wasn’t working. Coffee machine not working. Easy to walk to restaurants. Quiet.

Reviewed on Aug. 24, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was CA $1,482, price is now CA $1,143 per person
CA $1,143
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.4/10 Very Good! (1,345 reviews)
Great dog friendly location. Nice room

Reviewed on Aug. 30, 2025

Renaissance Pittsburgh Hotel

Renaissance Pittsburgh Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,838, price is now CA $1,437 per person
CA $1,437
per person
Oct 16 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Pittsburgh (PIT)
9/10 Wonderful! (1,010 reviews)
Location was excellent for PNC park

Reviewed on Sep. 1, 2025

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Price was CA $2,264, price is now CA $1,790 per person
CA $1,790
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)
Rooms very clean and nice. Every person I encountered was friendly and accomodating. Didn’t like paying $65 for valet parking though.

Reviewed on Aug. 30, 2025

Where to stay in Shadyside

Find the best Shadyside areas and neighborhoods for the activities you enjoy most. Learn more about Shadyside
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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

Shadyside Hotel Deals

Mansions on Fifth Hotel

Mansions on Fifth Hotel

4 out of 5
5105 Fifth Avenue, Pittsburgh, PA
The price is CA $246 per night from Sep 2 to Sep 3
CA $246
CA $281 total
Sep 2 - Sep 3
includes taxes & fees
Mansions on Fifth Hotel
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 $208 per night from Sep 28 to Sep 29
CA $208
CA $237 total
Sep 28 - Sep 29
includes taxes & fees
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 $219 per night from Sep 29 to Sep 30
CA $219
CA $249 total
Sep 29 - Sep 30
includes taxes & fees
Omni William Penn Hotel
See all 1,782 properties in Shadyside
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
Family Vacations
Family Vacations

Frequently asked questions

How much does a Shadyside vacation package cost?
From just CA $987. 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.

Discover the most popular places to visit in Shadyside

UPMC Shadyside

Though UPMC Shadyside might be what brings you to town, perhaps you'll have a chance to explore more of Pittsburgh while you are here.

UPMC Shadyside

Things to do

Pittsburgh, PA: Sandcastle Waterpark Entry Ticket

Pittsburgh, PA: Sandcastle Waterpark Entry Ticket

CA $43
per adult
Pittsburgh, PA: Sandcastle Waterpark Entry Ticket
Visit beautiful shopping and dining complex in your private tour

Private City Kickstart Tour: Tokyo

CA $186
per adult
100% of travellers recommend
Private City Kickstart Tour: Tokyo
Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

CA $76
per adult
Pittsburgh Pirates Baseball Game at PNC Park
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.