South Shore Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in South Shore

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
Price was CA $1,178, price is now CA $954 per person
CA $954
per person
Jul 7 - Jul 10
found 2 days ago
Roundtrip non-stop flight included
Thunder Bay (YQT) to Pittsburgh (PIT)
8.2/10 Very Good! (3,459 reviews)
The Breakfast was amazing, fast, and perfectly done service was great and every person was helpful and nice the room could have been cleaner

Reviewed on Apr 10, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was CA $2,053, price is now CA $1,534 per person
CA $1,534
per person
Jun 4 - Jun 7
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8/10 Very Good! (255 reviews)
It is so good and affordable, and I would like to come back one day!

Reviewed on Apr 6, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $2,652, price is now CA $1,986 per person
CA $1,986
per person
Jun 4 - Jun 7
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.4/10 Very Good! (81 reviews)
The bed was very comfortable, the kitchen was great, the TV was nice but no local channels, I didn't use the washer/dryer but nice to have in the room. The only issue was road noise came through the large windows.

Reviewed on Mar 31, 2026

Hilton Garden Inn Pittsburgh University Place

Hilton Garden Inn Pittsburgh University Place

3 out of 5
Central Oakland
Price was CA $1,865, price is now CA $1,507 per person
CA $1,507
per person
Jun 4 - Jun 7
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.8/10 Excellent! (1,006 reviews)
Loved the location just that it was a LOUD hotel. Not sure if we were next to the service elevator but heard bangs, opening closing of doors all night!

Reviewed on Apr 6, 2026

The Colonial Mt. Lebanon by Luxe PGH

The Colonial Mt. Lebanon by Luxe PGH

3 out of 5
Mount Lebanon
Price was CA $2,036, price is now CA $1,684 per person
CA $1,684
per person
Jun 4 - Jun 7
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
2/10 (2 reviews)

Where to stay in South Shore

Find the best South Shore areas and neighborhoods for the activities you enjoy most. Learn more about South Shore
Downtown Pittsburgh

Downtown Pittsburgh

2 out of top 10 points of interest in this area
4.5/5(190 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

South Shore Hotel Deals

Sheraton Pittsburgh Hotel at Station Square

Sheraton Pittsburgh Hotel at Station Square

3.5 out of 5
300 West Station Square Drive Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $234 per night from Apr 26 to Apr 27
CA $234
CA $267 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (1,056 reviews)
Clean room & good staff. I liked the location, but some people may not like the trains going by. My only complaint was the noise from the room Nextdoor. The connecting door although closed and locked did not block the voices from next door. Also the heat/air was very loud. The view was great and ...

Reviewed on Apr 10, 2026

Sheraton Pittsburgh Hotel at Station Square
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 $211 per night from Apr 21 to Apr 22
CA $211
CA $240 total
Apr 21 - Apr 22
includes taxes & fees
8.2/10 Very Good! (3,463 reviews)
The Breakfast was amazing, fast, and perfectly done service was great and every person was helpful and nice the room could have been cleaner

Reviewed on Apr 10, 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 $243 per night from Apr 30 to May 1
CA $243
CA $276 total
Apr 30 - May 1
includes taxes & fees
9.2/10 Wonderful! (1,983 reviews)
Absolutely gorgeous hotel. Incredibly clean and quiet, and all around amazing. My only complaint is that the "bouncer" for the speakeasy was rude. He at one point told the lady next to me that we needed to "calm down" because we were laughing. It was saint Patrick's day weekend and the other guests ...

Reviewed on Apr 6, 2026

Omni William Penn Hotel
See all 2,012 properties in South Shore
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 South Shore vacation package cost?
Less than you might think — from just CA $954, actually! By combining hotels, flights and car rentals into a custom-built travel package, your South Shore escape is just clicks away.
How do I get a cheap travel package to South Shore?
One of the easiest ways to save dollars (and time) is to combine your bookings with Expedia. Hotels, flights, rental cars and activities — we've got everything you need. Pick the combination that suits your style and see your savings stack up. Of course, a package deal is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 properties around the globe, which lets you customize your South Shore vacation.
Where should I stay in South Shore?
Urban explorers come from every corner of the globe to experience Acrisure Stadium and PNC Park in South Shore. Stay near these fantastic attractions to make sightseeing a breeze.
What are the top hotels in South Shore?
When it comes to welcoming places to stay in South Shore, you can't beat Sheraton Pittsburgh Hotel at Station Square. Be sure to browse its deals and land a bargain.
How far in advance should I book my South Shore vacation?
Earlier is always better. Airlines generally release flight tickets up to a year in advance, and this is when you can score some rock-bottom prices. Just been told you should take some vacation time next month? That's alright! Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia South Shore travel package include?
Flights, hotels and a shiny set of wheels for all your road trip adventures. Simply pick and choose your preferred bundle and gain access to great discounts. Once you've made your booking, add on a couple of tours and experiences and watch your savings grow. When it comes to creating your South Shore break, you're in charge!
What should I know before booking a South Shore travel package?
Locking in all the parts of your getaway together is a smart way to save. Bundle your flights, car rentals and hotels into a tidy package. But it's not just hotels. Expedia has all sorts of properties, including vacation rentals like beachfront villas and serviced residences. Your choices are almost endless!
Can I choose my airline with a South Shore Expedia vacation package?
Expedia has access to more than 550 partner airlines worldwide, so you certainly can. Just select your favorite carrier and put together the perfect South Shore trip.
If I'm not able to travel, can I cancel my South Shore vacation package?
Because we know life can throw you a few curveballs, the answer is yes. For further information, check out our Customer Service Portal. But generally speaking, if you've booked your South Shore vacation package in the last 24 hours, you may be able to cancel or change it for free. Your airline, hotel or car rental company may impose a fee if you made your booking a while ago.

Discover the most popular places to visit in South Shore

Monongahela Incline

Monongahela Incline

4.5/5(23 reviews)

Spectacular views of the Pittsburgh cityscape await at the top of the steepest funicular railway in the United States.

Monongahela Incline

Things to do

Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

CA $40
per adult
80% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
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 $67
per adult
Whiskey Rebellion & Prohibition 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.