Shadyside Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Shadyside

Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was CA $949, price is now CA $800 per person
CA $800
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Pittsburgh (PIT)
7.8/10 Good! (203 reviews)
Clean and very cozy

Reviewed on Feb 1, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,647, price is now CA $1,293 per person
CA $1,293
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay.

Reviewed on Jan 10, 2026

Ramada by Wyndham Butler/Tesla Biohealing Resort

Ramada by Wyndham Butler/Tesla Biohealing Resort

2.5 out of 5
Price was CA $1,472, price is now CA $1,206 per person
CA $1,206
per person
Mar 15 - Mar 22
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Pittsburgh (PIT)
7.8/10 Good! (109 reviews)
Everything is brand new, awesome pillows and mattresses! Parking close to room. The FLOOR in my room was cold, my only negative.

Reviewed on Feb 1, 2026

Hilton Garden Inn Pittsburgh Area Beaver Valley, PA

Hilton Garden Inn Pittsburgh Area Beaver Valley, PA

3 out of 5
Price was CA $1,554, price is now CA $1,321 per person
CA $1,321
per person
Mar 15 - Mar 22
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Pittsburgh (PIT)
9/10 Wonderful! (371 reviews)
Rverything was top tier!

Reviewed on Feb 1, 2026

DoubleTree by Hilton Pittsburgh - Cranberry

DoubleTree by Hilton Pittsburgh - Cranberry

4 out of 5
Price was CA $1,701, price is now CA $1,466 per person
CA $1,466
per person
Mar 15 - Mar 22
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Pittsburgh (PIT)
8.8/10 Excellent! (913 reviews)
Breakfast was delicious and the entire stay was great! The kids especially loved the indoor pool!

Reviewed on Jan 19, 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 which includes a bridge and a river or creek

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
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (999 reviews)
Fantastic property in a great location...if you like historical buildings and old school hotels then this one will not disappoint...

Reviewed on Jan 25, 2026

Get rates
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 $164 per night from Feb 12 to Feb 13
CA $164
CA $187 total
Feb 12 - Feb 13
includes taxes & fees
8.2/10 Very Good! (3,396 reviews)
Beautiful hotel. So close to downtown. Loved it.

Reviewed on Feb 2, 2026

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 $218 per night from Feb 12 to Feb 13
CA $218
CA $249 total
Feb 12 - Feb 13
includes taxes & fees
9/10 Wonderful! (1,943 reviews)
The only draw back was not having coffee available for early morning event we attended.

Reviewed on Feb 1, 2026

Omni William Penn Hotel
See all 1,936 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 $800. 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
Make new friends as you learn the exciting history of whiskey in Pittsburgh

Whiskey Rebellion & Prohibition Tour

CA $68
per adult
Whiskey Rebellion & Prohibition Tour
Pittsburgh: Beauty of the Burgh Bike Tour

Pittsburgh: Beauty of the Burgh Bike Tour

CA $82
per adult
94% of travellers recommend
Pittsburgh: Beauty of the Burgh Bike 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.