Shadyside Vacation Packages

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Top Holiday Package Deals in Shadyside

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
per person
Sep 19 - Sep 22
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8/10 Very Good! (2,984 reviews)
The employees were excellent. The restaurant & Bar area was very commentating. Clean lobby rooms were clean .

Reviewed on Aug. 2, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
per person
Sep 19 - Sep 22
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
Location, location, location. The property layout is super convenient with easy access to the convention center and local amenities. Like many properties, I felt the room was not as updated and fresh as the public areas were. Check-in was extremely fast and efficient. The value is in the proximity to the freeway and downtown life.

Reviewed on Jun. 22, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
per person
Sep 19 - Sep 22
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.4/10 Very Good! (1,353 reviews)
Great hotel with a very friendly staff

Reviewed on Jul. 28, 2025

Hilton Garden Inn Pittsburgh Downtown

Hilton Garden Inn Pittsburgh Downtown

3 out of 5
Downtown Pittsburgh
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Regina (YQR) to Pittsburgh (PIT)
9/10 Wonderful! (1,029 reviews)
Quality options for dinner nearby, bed was nice

Reviewed on Jul. 28, 2025

Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
per person
Sep 19 - Sep 22
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
9/10 Wonderful! (1,574 reviews)
Parking was a nightmare.

Reviewed on Aug. 3, 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

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 $164 per night from Aug 17 to Aug 18
CA $164
CA $187 total
Aug 17 - Aug 18
includes taxes & fees
8/10 Very Good! (2,971 reviews)
"The employees were excellent. The restaurant & Bar area was very commentating. Clean lobby rooms were clean ."

Reviewed on Aug. 2, 2025

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 $197 per night from Aug 20 to Aug 21
CA $197
CA $225 total
Aug 20 - Aug 21
includes taxes & fees
9/10 Wonderful! (1,577 reviews)
"The experience is easy and beautiful from the beginning, parking, checking in, baggage, and service. The room was clean and beautiful, great climate control, fluffy towels and the best fleece-lined robes are available in the room. The two beds offered both a more firm mattress and one had a softer ..."

Reviewed on Jul. 30, 2025

Omni William Penn Hotel
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
453 Boulevard of the Allies, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Aug 10 to Aug 11
CA $175
CA $203 total
Aug 10 - Aug 11
includes taxes & fees
8.2/10 Very Good! (1,334 reviews)
"Great hotel with a very friendly staff"

Reviewed on Jul. 28, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,755 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.
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Frequently asked questions

How much does a Shadyside vacation package cost?
From just CA $793. 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 Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

CA $18
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
Pittsburgh: Golden Triangle Guided Walking Tour at Sunset

Pittsburgh: Golden Triangle Guided Walking Tour at Sunset

CA $38
per adult
Pittsburgh: Golden Triangle Guided Walking Tour at Sunset
Step into the shadows and discover the haunting tales of our city's past.

Pittsburgh Ghosts Steel City Haunted Tour

CA $36
per adult
100% of travellers recommend
Pittsburgh Ghosts Steel City Haunted Tour
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.