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.
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
CA $863
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.2/10 Very good! (3,678 reviews)
Hotel was clean and the staff was great. Location is key for walking to everything
Reviewed on Aug 11, 2026
Stay Pittsburgh
Downtown Pittsburgh
CA $1,202
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8/10 Very good! (314 reviews)
Some confusion on my end with paying the deposit, as I thought I was paying for my room a second time, but the host was quick to clear it up. Another pleasant stay at this clean and quiet property.
Reviewed on Aug 9, 2026
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
2 out of top 10 points of interest in this area
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.
North Shore
2 out of top 10 points of interest in this area
Heinz Field, PNC Park, and The Andy Warhol Museum await in this vibrant area, connected to Downtown Pittsburgh by the iconic Roberto Clemente, Andy Warhol, and Rachel Carson Bridges. Enjoy easy access to two light rail stations.
Oakland
1 out of top 10 points of interest in this area
Academic and healthcare hub, Oakland boasts museums, shopping venues, and diverse dining options along Forbes and Fifth Avenue. Explore historic districts and easily navigate the area via the distinctive city steps and public transportation.
North Side
1 out of top 10 points of interest in this area
If you're spending time in North Side, check out sights like PNC Park or Acrisure Stadium and hop on the metro to see more the city at North Side Station or Allegheny Station.
Mount Washington
Consider a visit to Ohio River Valley and take some time to enjoy the abundant dining options during your time in Mount Washington. If you want to see more of the city, jump on the metro at South Hills Junction Station or Palm Garden Station.
South Shore Hotel Deals
Sheraton Pittsburgh Hotel at Station Square
300 West Station Square Drive Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $237
CA $270 total
Aug 20 - Aug 21
includes taxes & fees
9/10 Wonderful! (1,138 reviews)
"The front desk staff are very friendly and helpful. Housekeeping did an excellent job with cleaning. Nice to have coffee in the room. We had a wonderful stay and appreciate having a spotless room and comfortable beds and a very nice tv. Room is also spacious. With happy friendly staff. Our only recommendations ..."
Reviewed on Aug 10, 2026
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $172
CA $197 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very good! (3,751 reviews)
"Hotel was clean and the staff was great. Location is key for walking to everything"
Reviewed on Aug 11, 2026
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
CA $166
CA $189 total
Sep 2 - Sep 3
includes taxes & fees
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.
Frequently asked questions
How much does a South Shore vacation package cost?
Less than you might think — from just CA $863, 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.
Stay near popular South Shore attractions
Station Square
8.6/10 (1,102 reviews)
You can do some window-shopping at Station Square during your trip to Pittsburgh. Experience the acclaimed theater scene and entertainment choices in this vibrant area.
Monongahela Incline
9.0/10 (402 reviews)
Spectacular views of the Pittsburgh cityscape await at the top of the steepest funicular railway in the United States.
Highmark Stadium
8.6/10 (12 reviews)
Catch an event at Highmark Stadium during your trip to Pittsburgh. Amble around this vibrant area's riverfront or attend a sporting event.
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
CA $73
per adult
100% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
CA $41
per adult
90% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
CA $46
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.