South Shore Vacations from $526

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Your South Shore Vacation

Avoid the hassle of travel planning with a South Shore vacation package. With all the details organized before you go away, all that's left for you to do is enjoy this riverside neighborhood's cycling, views and walking. Start your trip to South Shore by heading to nearby attractions such as Acrisure Stadium, University of Pittsburgh and PNC Park. Stop daydreaming and start doing. When it's time to book your next vacation to South Shore, Expedia is here to help.

The Latest South Shore Vacation Packages

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

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $721, price is now $526 per person
$526
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
8/10 Very Good! (310 reviews)
Great job

Reviewed on Jul 26, 2026

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,100, price is now $738 per person
$738
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (3,662 reviews)
Hotel was very clean and in a wonderful area of the city. Close to restaurants and attractions.

Reviewed on Jul 30, 2026

Hyatt House Pittsburgh/Bloomfield/Shadyside

Hyatt House Pittsburgh/Bloomfield/Shadyside

3 out of 5
Bloomfield
Price was $739, price is now $549 per person
$549
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
9/10 Wonderful! (1,005 reviews)

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $1,054, price is now $836 per person
$836
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,583 reviews)

Crowne Plaza Suites Pittsburgh South by IHG

Crowne Plaza Suites Pittsburgh South by IHG

3.5 out of 5
Price was $813, price is now $657 per person
$657
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 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
A yellow bridge over a river with a cityscape in the background.

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.

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
$170 nightly
The price is $194 total per night from Aug 20 to Aug 21
$194 total
Aug 20 - Aug 21
Total with taxes and fees
9/10 Wonderful! (1,125 reviews)
"Easy check in and check out. Only negative is that check in wasn’t until 4 pm and check out was 11 am, should be more hours"

Reviewed on Jul 29, 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
$125 nightly
The price is $142 total per night from Aug 30 to Aug 31
$142 total
Aug 30 - Aug 31
Total with taxes and fees
8.2/10 Very Good! (3,665 reviews)
"Hotel was very clean and in a wonderful area of the city. Close to restaurants and attractions."

Reviewed on Jul 30, 2026

Wyndham Grand Pittsburgh Downtown
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $154 total per night from Aug 23 to Aug 24
$154 total
Aug 23 - Aug 24
Total with taxes and fees
The Landing Hotel at Rivers Casino
See all 2,061 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
Kid Friendly Vacations
Kid Friendly Vacations

Stay near popular South Shore attractions

A bridge with ornate towers and a cityscape in the background.

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.
See properties

Things to do

Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

$47
per adult
100% of travellers recommend
Pittsburgh Pirates Baseball Game at PNC Park
Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

$29
per adult
90% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
This tour is the best tour for sports fans! Big fun guaranteed!

Black & Gold Pittsburgh History Tour for Sports Fans

$33
per adult
Black & Gold Pittsburgh History Tour for Sports Fans
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.