Fairywood Vacations from $482

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The Latest Fairywood Vacation Packages

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

DoubleTree by Hilton Pittsburgh - Cranberry

$482

per person

Dec 5 - Dec 8

found 3 hours ago

Roundtrip flight included

New York (NYC) to Pittsburgh (PIT)

8.8/10 Excellent! (1,002 reviews)

Stay Pittsburgh

Downtown Pittsburgh

$568

per person

Dec 5 - Dec 7

found 20 hours ago

Roundtrip flight included

New York (NYC) to Pittsburgh (PIT)

8/10 Very Good! (332 reviews)

Fairmont Pittsburgh

Downtown Pittsburgh

$984

per person

Nov 5 - Nov 10

found 23 hours ago

Roundtrip flight included

Los Angeles (LAX) to Pittsburgh (PIT)

8.8/10 Excellent! (1,003 reviews)

The Oaklander Hotel, Autograph Collection

Oakland

$715

per person

Dec 5 - Dec 8

found 3 hours ago

Roundtrip flight included

New York (NYC) to Pittsburgh (PIT)

9.2/10 Wonderful! (833 reviews)

Oakmont Inn

Plum

$761

per person

Nov 20 - Nov 22

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Pittsburgh (PIT)

10/10 Exceptional! (38 reviews)

Very quiet and incredibly clean! We absolutely loved the place!

Reviewed on Sep 27, 2026

Where to stay in Fairywood

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

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.

Fairywood Hotel Deals

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA

Fully refundableReserve now, pay when you stay

$124 nightly

$141 total

Oct 12 - Oct 13

Total with taxes and fees

Pittsburgh Marriott City Center

112 Washington Pl Pittsburgh PA

Fully refundableReserve now, pay when you stay

$152 nightly

$173 total

Oct 16 - Oct 17

Total with taxes and fees

8.2/10 Very Good! (1,329 reviews)

"The parking is very expensive"

Reviewed on Sep 27, 2026

The Landing Hotel at Rivers Casino

757 Casino Dr Pittsburgh PA

Fully refundableReserve now, pay when you stay

$136 nightly

$155 total

Oct 28 - Oct 29

Total with taxes and fees

See all 2,045 properties in Fairywood

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.