Westwood Vacation Packages

Plan, book, travel with confidence
Better together
Save up to CA $4,200 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

Top Holiday Package Deals in Westwood

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

Hyatt House Pittsburgh/Bloomfield/Shadyside

Bloomfield

CA $1,245

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Pittsburgh (PIT)

9/10 Wonderful! (1,012 reviews)

Excellent stay! Thank you to all the staff!

Reviewed on Aug 5, 2026

Stay Pittsburgh

Downtown Pittsburgh

CA $1,250

per person

Oct 9 - Oct 11

found 9 hours ago

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

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

CA $1,620

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Pittsburgh (PIT)

8.6/10 Excellent! (1,000 reviews)

The staff at the Westin was extremely helpful and proactive. The initial room they gave us had some issues, including a smoke-like smell (not cigarette smoke). As soon as we notified reception, someone handled it extremely professionally, and within minutes we were moved to a much better room.

Reviewed on Aug 3, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

CA $1,417

per person

Oct 9 - Oct 11

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Pittsburgh (PIT)

8.6/10 Excellent! (1,581 reviews)

Placemakr Downtown Pittsburgh at The Pennsylvanian

Downtown Pittsburgh

CA $1,752

per person

Oct 9 - Oct 11

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Pittsburgh (PIT)

8.6/10 Excellent! (187 reviews)

Where to stay in Westwood

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

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.

Westwood 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

The Landing Hotel at Rivers Casino

757 Casino Dr Pittsburgh PA

Fully refundableReserve now, pay when you stay

CA $167

CA $191 total

Aug 23 - Aug 24

includes taxes & fees

9.4/10 Exceptional! (2,123 reviews)

"Very friendly staff convenient location walking distance to PNC park overall amazing place"

Reviewed on Aug 7, 2026

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! (2,061 reviews)

"The hotel was beautiful, but the experience was lackluster. Had a very confusing and frustrating conversation with the valets when I first arrived — the staff the rest of the time was helpful and friendly. Our room was clean, but the shower backed up and our bed was missing a pillow and a fitted ..."

Reviewed on Aug 7, 2026

See all 2,051 properties in Westwood

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.