Windgap Vacations from $481

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The Latest Windgap Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A brick building with a large arched entrance labeled "STAYPGH".
    Dec 26 - Dec 28

    Stay Pittsburgh + Flight

    Downtown Pittsburgh
    2 nights
    2.0 star property
    8.0/10 - Very good (346 reviews)
    Roundtrip • New York (EWR) - Pittsburgh (PIT)
    EWR - PIT • Nonstop PIT - EWR • Nonstop
    $584
    $481
    per traveler
    found 2 hours ago
    Stay Pittsburgh
  • A reception area with a tiled floor, two patterned armchairs, a desk with a reception sign, and a large mirror.
    Dec 29 - Jan 3

    Americas Best Value Inn Pittsburgh Airport + Flight

    Coraopolis
    5 nights
    2.0 star property
    6.6/10 - (1,001 reviews)
    Roundtrip • Atlanta (ATL) - Pittsburgh (PIT)
    ATL - PIT • Nonstop PIT - ATL • Nonstop
    $629
    $481
    per traveler
    found 1 day ago
    Americas Best Value Inn Pittsburgh Airport
  • A multi-story hotel with a brick facade, large windows, and a flagpole with an American flag.
    Feb 5 - Feb 7

    Hampton Inn & Suites Pittsburgh-Downtown + Flight

    Downtown Pittsburgh
    2 nights
    2.5 star property
    9.4/10 - Exceptional (1,368 reviews)
    "Well, there was no working water in our shower. Kind of a bummer to find out about when you are rushing to an event at Pitt early in the morning. Not enough time to fix it, so the use of the room was all waste."
    Reviewed November 7, 2026
    Roundtrip • New York (EWR) - Pittsburgh (PIT)
    EWR - PIT • Nonstop PIT - EWR • Nonstop
    $725
    $602
    per traveler
    found 1 day ago
    Hampton Inn & Suites Pittsburgh-Downtown
  • A modern kitchen with stainless steel appliances, a marble countertop, and a view to the living area.
    Dec 19 - Dec 21

    Landing Furnished Apartments near UPMC Shadyside + Flight

    Squirrel Hill
    2 nights
    3.0 star property
    Roundtrip • New York (JFK) - Pittsburgh (PIT)
    JFK - PIT • Nonstop PIT - JFK • Nonstop
    $973
    $808
    per traveler
    found 1 day ago
    Landing Furnished Apartments near UPMC Shadyside
  • A spacious hotel lobby with multiple seating areas, a bar, and large windows allowing natural light.
    Dec 18 - Dec 21

    DoubleTree by Hilton Pittsburgh - Cranberry + Flight

    Mars
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,002 reviews)
    "I unfortunately got bed bug bites while being there. When I called to inform them to ensure the next guest wasn’t affected, they merely took information for their incident report."
    Reviewed November 7, 2026
    Roundtrip • New York (NYC) - Pittsburgh (PIT)
    JFK - PIT • Nonstop PIT - JFK • Nonstop
    $625
    $535
    per traveler
    found 2 days ago
    DoubleTree by Hilton Pittsburgh - Cranberry

Where to stay in Windgap

Find the best Windgap areas and neighborhoods for the activities you enjoy most.
A yellow bridge over a river with a cityscape in the background.

Downtown Pittsburgh

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 city skyline at dusk with illuminated buildings, a prominent bridge, and a river.
Photo by TM
Open Photo by TM

North Shore

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.

A dinosaur statue in front of a historic building with inscriptions.

Oakland

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 building with a large sign reading 'THE TERMINAL' and storefronts for 'posman books' and 'solidcore.'
Photo by TM
Open Photo by TM

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 bridge with illuminated lights reflecting on the water, a city skyline in the background, and a smokestack emitting smoke.

North Side

If you're spending time in North Side, check out sights like PNC Park or Acrisure Stadium and hop on the metro to see more the city at North Side Station or Allegheny Station.

Windgap Hotel Deals

A lobby with a fireplace, seating area, and a television mounted above it.

Holiday Inn Express & Suites Pittsburgh West - Greentree by IHG

Holiday Inn Express & Suites Pittsburgh West - Greentree by IHG
2.5 star property
2.9 mi from Windgap
8.6 out of 10, Excellent, (1,200 reviews)
$79 nightly
The price is $90
Dec 10 - Dec 11
Total with taxes and fees
Holiday Inn Express & Suites Pittsburgh West - Greentree by IHG
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.
See all properties in Windgap
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.