South Shore Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Holiday Package Deals in South Shore
Price found within the past 48 hours. Click for updated prices.
Hyatt House Pittsburgh/Bloomfield/Shadyside
Bloomfield
CA $1,230
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
9/10 Wonderful! (1,019 reviews)
Thank you Lovemerry for your professionalism and kindness!!
Great location near Shadyside and a half mile walk to the Shady Grove!!
Reviewed on Aug 27, 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.
Shadyside
Victorian mansions and modern apartments create a diverse residential atmosphere. Explore upscale stores on Walnut Street, dine at local eateries like Pamela's Diner, and easily walk between the three business corridors. Public transportation is accessible.
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 $246
CA $281 total
Sep 6 - Sep 7
includes taxes & fees
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $186
CA $212 total
Aug 30 - Aug 31
includes taxes & fees
8.4/10 Very good! (3,724 reviews)
"wish there was on site parking, instead of valet parking or having to find a parking garage to park in"
Reviewed on Aug 27, 2026
Pittsburgh Marriott City Center
112 Washington Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $187
CA $213 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very good! (1,320 reviews)
"Clean room. Delicious breakfast!"
Reviewed on Aug 27, 2026
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 $994, 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.