Windgap Vacation Packages

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Top Holiday Package Deals in Windgap

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

Stay Pittsburgh

Downtown Pittsburgh

CA $1,250

per person

Oct 9 - Oct 11

just found

Roundtrip non-stop flight included

Toronto (YTO) to Pittsburgh (PIT)

8/10 Very good! (313 reviews)

Very responsive, great location, awesome hosts! 10/10 would recommend.

Reviewed on Jul 31, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

CA $1,417

per person

Oct 9 - Oct 11

just found

Roundtrip non-stop flight included

Toronto (YTO) to Pittsburgh (PIT)

8.6/10 Excellent! (1,581 reviews)

I nice and clean.

Reviewed on Aug 6, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Downtown Pittsburgh

CA $1,752

per person

Oct 9 - Oct 11

just found

Roundtrip non-stop flight included

Toronto (YTO) to Pittsburgh (PIT)

8.6/10 Excellent! (173 reviews)

Sheraton Pittsburgh Hotel at Station Square

South Shore

CA $2,715

per person

Oct 9 - Oct 11

just found

Roundtrip non-stop flight included

Toronto (YTO) to Pittsburgh (PIT)

9/10 Wonderful! (1,126 reviews)

Pittsburgh Marriott City Center

Downtown Pittsburgh

CA $1,666

per person

Oct 9 - Oct 11

just found

Roundtrip non-stop flight included

Toronto (YTO) to Pittsburgh (PIT)

8.2/10 Very good! (1,327 reviews)

Where to stay in Windgap

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

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

North Side

1 out of top 10 points of interest in this area

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.

A river with a bridge, a van on the road, and buildings in the background.

Mount Washington

Consider a visit to Ohio River Valley and take some time to enjoy the abundant dining options during your time in Mount Washington. If you want to see more of the city, jump on the metro at South Hills Junction Station or Palm Garden Station.

Windgap Hotel Deals

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA

Fully refundableReserve now, pay when you stay

CA $173

CA $198 total

Sep 1 - Sep 2

includes taxes & fees

8.2/10 Very good! (3,715 reviews)

"Definitely good.. ………………………….."

Reviewed on Aug 7, 2026

The Landing Hotel at Rivers Casino

757 Casino Dr Pittsburgh PA

Fully refundableReserve now, pay when you stay

CA $167

CA $190 total

Aug 23 - Aug 24

includes taxes & fees

Omni William Penn Hotel

530 William Penn Place Pittsburgh PA

Fully refundableReserve now, pay when you stay

CA $265

CA $302 total

Aug 9 - Aug 10

includes taxes & fees

9.2/10 Wonderful! (2,059 reviews)

"Our rooms were very clean and beautiful. Loved the decorative touch of the crown molding in the sleeping rooms. The staff were incredible - from the Valet and Bellman to the restaurant servers ... Haris in the restaurant is a MUST request. He is exceptionally friendly and attentive and made our meals ..."

Reviewed on Aug 7, 2026

See all 2,041 properties in Windgap

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.