South Shore Vacation Packages

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Top Holiday Package Deals in South Shore

Price found within the past 48 hours. Click for updated prices.
The Maverick by Kasa

The Maverick by Kasa

3 out of 5
East Liberty
per person
Aug. 18 - Aug. 23
found 17 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
8.6/10 Excellent! (350 reviews)
The historic architect remains, nice sleek decor design nice staff.

Reviewed on May 27, 2024

Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
per person
Aug. 18 - Aug. 23
found 23 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
9/10 Wonderful! (1,326 reviews)
No clear smoking area. Shower set up was cheap looking for such a beautiful hotel.

Reviewed on May 28, 2024

Wyndham Pittsburgh University Center

Wyndham Pittsburgh University Center

3.5 out of 5
Oakland
per person
Aug. 18 - Aug. 23
found 17 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
7.6/10 Good! (1,304 reviews)
Property was under construction so a few hiccups in the area of on site dining and occasional elevator issues. Staff was accommodating.

Reviewed on May 28, 2024

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
per person
Aug. 18 - Aug. 23
found 23 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
8.4/10 Very Good! (1,001 reviews)
The convenience of having the Marriott next to arena was great. Access from the parkway off the exit was simply the best . Decreases the travel time and eliminates stress in avoiding city traffic. The staff at the hotel were very nice and check in efficient and took very little time. The hotel room was old and could use a face lift . It was very clean .! All in all it was a great experience staying at this hotel site.

Reviewed on May 26, 2024

EVEN Hotel Pittsburgh Downtown, an IHG Hotel

EVEN Hotel Pittsburgh Downtown, an IHG Hotel

4 out of 5
Downtown Pittsburgh
per person
Aug. 18 - Aug. 23
found 23 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
8.4/10 Very Good! (1,002 reviews)
Very convenient location downtown. A little beat up but pretty clean. Staff was very courteous. Cute little bar area too.

Reviewed on May 27, 2024

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 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 hotel + flight trips 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 $207 per night from May 29 to May 30
CA $207
CA $236 total
includes taxes & fees
May 29 - May 30
8.4/10 Very Good! (1,005 reviews)
"Beautiful hotel and view. Easy check in. The absolute only issue was the smell in the room which i believe was the ac unit. Mildew. But got past it. Area was great"

Reviewed on May 27, 2024

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 $184 per night from May 29 to May 30
CA $184
CA $210 total
includes taxes & fees
May 29 - May 30
7.4/10 Good! (2,725 reviews)
"Fantastic location, walkable to a lot of restaurants and the stadiums. We had a beautiful view of the river. The only complaint was the hotel was extremely busy the weekend and we had to wait in long lines for the elevator. Walls seemed thin too, we could hear our neighbors alarm clock."

Reviewed on May 27, 2024

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 $265 per night from Jun. 19 to Jun. 20
CA $265
CA $302 total
includes taxes & fees
Jun 19 - Jun 20
9/10 Wonderful! (1,333 reviews)
"A classic hotel conveniently situated in the heart of downtown Pittsburgh. Its elegance made our visit extra special. We did not know much about the hotel before we booked it, but after staying there, we will definitely return to the Omni William Penn on any future visits to the Iron City."

Reviewed on May 27, 2024

Omni William Penn Hotel
See all 1,570 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.

Explore other types of vacation packages

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 $943, 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

Image for Monongahela Incline

Monongahela Incline

4.5/5(22 reviews)

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

Monongahela Incline
Image for PNC Park

PNC Park

4.5/5(67 reviews)

Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.

PNC Park
Image for Acrisure Stadium

Acrisure Stadium

4.5/5(94 reviews)

Giant ketchup bottles tilt onto the scoreboard to celebrate touchdowns in this innovative riverside football arena at the heart of Pittsburgh sports.

Acrisure Stadium

Things to do

Image for Pittsburgh to Logstown Settler's History: A Self-Guided Driving Tour

Pittsburgh to Logstown Settler's History: A Self-Guided Driving Tour

CA $9
Per adult
Pittsburgh to Logstown Settler's History: A Self-Guided Driving Tour
Image for Pittsburgh's Hidden Treasures Tour

Pittsburgh's Hidden Treasures Tour

CA $68
Per adult
Pittsburgh's Hidden Treasures Tour
See all activities in Pittsburgh

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.