Windgap Vacations from $328

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The Latest Windgap Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Americas Best Value Inn Pittsburgh Airport

Americas Best Value Inn Pittsburgh Airport

$328
per person
Oct 10 - Oct 12
found 11 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
6.6/10 (1,006 reviews)
Good but they give us room no clean then we had to ask for an other one

Reviewed on Aug 14, 2026

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

Downtown Pittsburgh
$403
per person
Sep 18 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.2/10 Very Good! (3,705 reviews)
We were in town for a baseball game. We were able to walk to the ball park and enjoy a comfortable place to stay after the game.

Reviewed on Aug 15, 2026

Stay Pittsburgh

Stay Pittsburgh

Downtown Pittsburgh
Save 100% on your flight
$773
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8/10 Very Good! (314 reviews)
Some confusion on my end with paying the deposit, as I thought I was paying for my room a second time, but the host was quick to clear it up. Another pleasant stay at this clean and quiet property.

Reviewed on Aug 9, 2026

DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

$554
per person
Oct 16 - Oct 18
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,112 reviews)
Hyatt House Pittsburgh/Bloomfield/Shadyside

Hyatt House Pittsburgh/Bloomfield/Shadyside

Bloomfield
$474
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
9/10 Wonderful! (1,008 reviews)
The hotel is a very short walk to UPMC Shadyside which is why I booked it. The breakfast was hot and delicious. There's a good variety and it's complete. There are places to eat and drink within half to three quarter miles that were an easy walk. And a diner only a couple blocks away.

Reviewed on Aug 16, 2026

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

Restaurant Row and scenic leafy parks lie along the ridge of a famous hill, where George Washington mapped the terrain for the British.

Windgap Hotel Deals

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$124 nightly
$141 total
Aug 30 - Aug 31
Total with taxes and fees
8.4/10 Very Good! (3,700 reviews)
"We were in town for a baseball game. We were able to walk to the ball park and enjoy a comfortable place to stay after the game."

Reviewed on Aug 15, 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
$135 nightly
$154 total
Aug 23 - Aug 24
Total with taxes and fees
The Landing Hotel at Rivers Casino
Omni William Penn Hotel

Omni William Penn Hotel

530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
$199 nightly
$227 total
Aug 30 - Aug 31
Total with taxes and fees
Omni William Penn Hotel
See all 2,017 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.

Things to do

Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

$48
per adult
100% of travellers recommend
Pittsburgh Pirates Baseball Game at PNC Park
Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

$29
per adult
90% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
This tour is the best tour for sports fans! Big fun guaranteed!

Black & Gold Pittsburgh History Tour for Sports Fans

$33
per adult
Black & Gold Pittsburgh History Tour for Sports Fans
See all activities in Pittsburgh
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.