Oakwood Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Oakwood

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

Find hotels in North Shore
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.

Find hotels in Oakland
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.

Find hotels in Strip District
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.

Find hotels in Shadyside

Oakwood Hotel Deals

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
₩165,750
₩188,955 total
Nov 2 - Nov 3
includes taxes & fees
8.4/10 Very Good! (3,845 reviews)
"Check in good, valet fantastic, hospitality terrible, no soap to wash hands in the room, no regular coffee, 1 wash rag in the room, place is convenient to downtown Pitt and clean"

Reviewed on Oct 11, 2026

Wyndham Grand Pittsburgh Downtown
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
₩169,878
₩193,661 total
Oct 12 - Oct 13
includes taxes & fees
9.4/10 Exceptional! (2,422 reviews)
"My fiancé and I love it here! That’s all"

Reviewed on Oct 10, 2026

The Landing Hotel at Rivers Casino
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

500 Mansfield Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
₩140,124
₩159,742 total
Nov 5 - Nov 6
includes taxes & fees
8.8/10 Excellent! (1,257 reviews)
"Noisy area. Older facility. No restaurants near by"

Reviewed on Oct 11, 2026

DoubleTree by Hilton Pittsburgh - Green Tree
See all 1,999 properties in Oakwood
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.