Brookline Vacations from $304

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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.
Hilton Garden Inn Pittsburgh University Place

Hilton Garden Inn Pittsburgh University Place

3 out of 5
Central Oakland
Price was $397, price is now $304 per person
$304
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.8/10 Excellent! (1,004 reviews)
Clean room and everyone was friendly

Reviewed on Nov 24, 2025

Hilton Garden Inn Pittsburgh Downtown

Hilton Garden Inn Pittsburgh Downtown

3 out of 5
Downtown Pittsburgh
Price was $521, price is now $393 per person
$393
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Miami (MIA) to Pittsburgh (PIT)
9/10 Wonderful! (1,151 reviews)
The hotel was clean and neat. The lobby furniture could use an update.

Reviewed on Dec 2, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $414, price is now $315 per person
$315
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Miami (MIA) to Pittsburgh (PIT)
8.4/10 Very Good! (1,385 reviews)
Room was perfect for the trip and clean and staff was very helpful

Reviewed on Nov 27, 2025

Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Price was $424, price is now $323 per person
$323
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Miami (MIA) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,253 reviews)
Great hotel, excellent location.

Reviewed on Nov 25, 2025

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Price was $474, price is now $368 per person
$368
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Miami (MIA) to Pittsburgh (PIT)
8/10 Very Good! (1,009 reviews)
The hotel room was fine but the cost for parking is astronomical.

Reviewed on Dec 3, 2025

Where to stay in Brookline

Find the best Brookline areas and neighborhoods for the activities you enjoy most. Learn more about Brookline
Downtown Pittsburgh which includes a bridge and a river or creek

Downtown Pittsburgh

2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)

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.

Find hotels in Downtown Pittsburgh

Brookline Hotel Deals

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $132 total per night from Dec 18 to Dec 19
$132 total
Dec 18 - Dec 19
Total with taxes and fees
8/10 Very Good! (3,233 reviews)
Good, as usual.

Reviewed on Dec 1, 2025

Wyndham Grand Pittsburgh Downtown
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
453 Boulevard of the Allies Pittsburgh PA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $123 total per night from Dec 21 to Dec 22
$123 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (1,400 reviews)
Customer Service

Reviewed on Dec 1, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $181 total per night from Jan 1 to Jan 2
$181 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9/10 Wonderful! (1,801 reviews)
Spacious clean room

Reviewed on Dec 4, 2025

Omni William Penn Hotel
See all 1,814 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Brookline

Mario Lemieux statue

PPG Paints Arena

Catch an event at PPG Paints Arena during your trip to Pittsburgh. Experience the acclaimed theater scene or attend a sporting event in this vibrant area.

PPG Paints Arena
PNC Park showing a city

PNC Park

Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.

PNC Park
Oakland featuring a garden

University of Pittsburgh

Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

University of Pittsburgh

Things to do

Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena

Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena

$72
per adult
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

$13
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
Pittsburgh Steelers Football Game at Acrisure Stadium

Pittsburgh Steelers Football Game at Acrisure Stadium

$452
per adult
Pittsburgh Steelers Football Game at Acrisure Stadium
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.