Brookline Vacation Packages 2026 from $452

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Your Brookline Vacation

Your next big journey is calling with a vacation package to Brookline. Relaxation, entertainment and nothing but great times — you're bound to find it in this neighborhood. Some popular nearby attractions to see during your trip to Brookline include Monongahela Incline, Duquesne Incline and Station Square. No matter your travel plans or budget, booking your ideal Brookline vacation is simple with Expedia.

The Latest Brookline Vacation Packages

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

Villagio Boutique Hotel

North Side

$452

per person

Jan 2 - Jan 4

found 1 day ago

Roundtrip flight included

New York (NYC) to Pittsburgh (PIT)

9.4/10 Exceptional! (164 reviews)

Easy check-in / check-out process. Appreciate the free parking in the lot beside the hotel. Large room (Alpine Suite) where we could relax in separate spaces

Reviewed on Oct 15, 2026

Stay Pittsburgh

Downtown Pittsburgh

$579

per person

Dec 19 - Dec 21

found 1 hour ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)

8/10 Very Good! (334 reviews)

Check in was rough online only. I couldn't reach anyone by phone, granted it was 10pm, but it took me forever to get through the process and then wait for a code to get into my room. Make sure you check in right when you get the text or email message.

Reviewed on Oct 17, 2026

Americas Best Value Inn Pittsburgh Airport

$539

per person

Dec 27 - Dec 31

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)

6.6/10 (1,005 reviews)

Holiday Inn Weirton - Steubenville Area by IHG

$634

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Pittsburgh (PIT)

8.4/10 Very Good! (354 reviews)

Sleek 2BR Downtown Retreat with Gym

Downtown Pittsburgh

$1,292

per person

Dec 4 - Dec 9

found 1 day ago

Roundtrip flight included

Houston (IAH) to Pittsburgh (PIT)

10/10 Exceptional! (10 reviews)

Perfect space for our family. Excellent communication regarding Pitt Marathon Weekend allowed us to plan our activities. Easy walk to Acrisure Stadium and north shore restaurants. Beautiful views of the city.

Reviewed on May 10, 2026

Where to stay in Brookline

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

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 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.

Brookline Hotel Deals

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA

Fully refundableReserve now, pay when you stay

$124 nightly

$141 total

Nov 3 - Nov 4

Total with taxes and fees

The Landing Hotel at Rivers Casino

757 Casino Dr Pittsburgh PA

Fully refundableReserve now, pay when you stay

$127 nightly

$144 total

Nov 15 - Nov 16

Total with taxes and fees

9.4/10 Exceptional! (2,463 reviews)

"Hotel was fine the casino security needs a little update on rules and regulations, they gave me misleading information that made me feel u easy about my whole stay."

Reviewed on Oct 19, 2026

DoubleTree by Hilton Pittsburgh - Green Tree

500 Mansfield Avenue Pittsburgh PA

Fully refundableReserve now, pay when you stay

$101 nightly

$115 total

Nov 8 - Nov 9

Total with taxes and fees

8.8/10 Excellent! (1,271 reviews)

"We didn’t have the remote control to watch TV. There was no heat. We were cold freezing all night. I couldn’t get any sleep. I was up all night. They didn’t fix the heat until about 11 o’clock when it was checkout time I would like a refund."

Reviewed on Oct 18, 2026

See all 1,963 properties in Brookline

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.