South Side Vacation Packages

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Top South Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
Price was CA $1,840, price is now CA $1,543 per person
CA $1,543
per person
May 1 - May 4
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,607 reviews)
One light was broken. The drawers did not close all the way. It was not the cleanest. The work out facilities were excellent. The size of the room and the staff were excellent. The location was excellent. I would stay there again.

Reviewed on Mar 13, 2026

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Price was CA $1,862, price is now CA $1,572 per person
CA $1,572
per person
May 1 - May 4
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.2/10 Very Good! (1,172 reviews)
Room was clean & very nice! Late night pizza in the lobby was huge bonus!

Reviewed on Mar 15, 2026

City Sights 2 Queen Beds Downtown Apt

City Sights 2 Queen Beds Downtown Apt

2 out of 5
Downtown Pittsburgh
Price was CA $2,169, price is now CA $1,897 per person
CA $1,897
per person
May 1 - May 4
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
6/10 (1 review)
2bedroom 2bathroom Apt Downtown Walk Anywhere

2bedroom 2bathroom Apt Downtown Walk Anywhere

2 out of 5
Downtown Pittsburgh
Price was CA $2,073, price is now CA $1,819 per person
CA $1,819
per person
May 1 - May 4
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
No reviews
2 Bedroom 2 Bath Apartment Heart of Downtown PIT

2 Bedroom 2 Bath Apartment Heart of Downtown PIT

2 out of 5
Downtown Pittsburgh
Price was CA $2,073, price is now CA $1,819 per person
CA $1,819
per person
May 1 - May 4
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
No reviews

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South Side Hotel Deals

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

2.5 out of 5
20 S 10th St Pittsburgh PA
Fully refundable
The price is CA $110 per night from Mar 18 to Mar 19
CA $110
CA $125 total
Mar 18 - Mar 19
includes taxes & fees
7.4/10 Good! (1,003 reviews)
Yes

Reviewed on Mar 15, 2026

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
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 $170 per night from Apr 1 to Apr 2
CA $170
CA $193 total
Apr 1 - Apr 2
includes taxes & fees
8.2/10 Very Good! (3,435 reviews)
Nice room. Not the newest of furnishings, but certainly was comfortable.

Reviewed on Mar 15, 2026

Wyndham Grand Pittsburgh Downtown
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
453 Boulevard of the Allies Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Mar 29 to Mar 30
CA $144
CA $167 total
Mar 29 - Mar 30
includes taxes & fees
8.4/10 Very Good! (1,475 reviews)
If it wasn't for the bartender being nice, we would have given this a lower review. Booked a king bed and was placed in a room with a single queen. When we complained they repeatedly tried to gaslight us as if we weren't capable of knowing a bed measurement. They were 1 hour late letting us in to ...

Reviewed on Mar 16, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,946 properties in South Side
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

Discover the most popular places to visit in South Side

PNC Park which includes a city

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
Mario Lemieux statue

PPG Paints Arena

5/5(80 reviews)

Catch an event at PPG Paints Arena during your trip to Pittsburgh. Experience the acclaimed theater scene or attend a sporting event in this vibrant area.

PPG Paints Arena
University of Pittsburgh in Pittsburgh, PA

University of Pittsburgh

4.5/5(36 reviews)

Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

University of Pittsburgh

What to do in South Side

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
Pittsburgh: Beauty of the Burgh Bike Tour

Pittsburgh: Beauty of the Burgh Bike Tour

CA $81
per adult
94% of travellers recommend
Pittsburgh: Beauty of the Burgh Bike Tour
See all activities in South Side

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