Highland Park Vacation Packages

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Top Holiday Package Deals in Highland Park

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

Hotel Indigo Pittsburgh University-Oakland by IHG

Oakland

CA $1,234

per person

Dec 3 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Pittsburgh (PIT)

8.6/10 Excellent! (1,005 reviews)

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

CA $1,776

per person

Dec 3 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Pittsburgh (PIT)

8.6/10 Excellent! (1,004 reviews)

Staff extremely helpful and friendly , bar on site great food and service

Reviewed on Sep 6, 2026

Etage Executive Living

Downtown Pittsburgh

CA $1,737

per person

Dec 3 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Pittsburgh (PIT)

9.2/10 Wonderful! (1,895 reviews)

The space, the design, the vibe having the gym down below, and the roof top access , full kitchen and location of the Etage make it perfect

Reviewed on Sep 12, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Downtown Pittsburgh

CA $1,612

per person

Dec 3 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Pittsburgh (PIT)

8.6/10 Excellent! (228 reviews)

Great place to stay!

Reviewed on Sep 9, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

CA $1,386

per person

Dec 3 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Pittsburgh (PIT)

8.6/10 Excellent! (1,639 reviews)

Where to stay in Highland Park

Find the best Highland Park areas and neighborhoods for the activities you enjoy most. Learn more about Highland Park

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.

A yellow bridge over a river, a weeping willow tree, and a modern building with glass windows.

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.

The Mellon Institute at Carnegie Mellon University with classical columns and a Gothic cathedral in the background.

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.

A street with a Starbucks and a plaza with colorful steps.

Strip District

Brimming with specialty shops, unique boutiques, and ethnic food purveyors, the Strip District offers a lively atmosphere with art studios, antique dealers, and the historic St. Stanislaus Kostka Church. Enjoy open-air markets and vibrant nightlife during summer months.

A courtyard with a fountain, brick walls, and trees.

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.

Highland Park Hotel Deals

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA

Fully refundableReserve now, pay when you stay

CA $198

CA $226 total

Oct 13 - Oct 14

includes taxes & fees

Pittsburgh Marriott City Center

112 Washington Pl Pittsburgh PA

Fully refundableReserve now, pay when you stay

CA $199

CA $227 total

Sep 20 - Sep 21

includes taxes & fees

DoubleTree by Hilton Pittsburgh - Green Tree

500 Mansfield Avenue Pittsburgh PA

Fully refundableReserve now, pay when you stay

CA $147

CA $167 total

Sep 20 - Sep 21

includes taxes & fees

8.8/10 Excellent! (1,197 reviews)

"Staff was nice"

Reviewed on Sep 13, 2026

See all 2,021 properties in Highland Park

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.