Brookline Vacations from $394

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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.
Traveler's Rest Hotel

Traveler's Rest Hotel

2 out of 5
South Side Flats
Price was $488, price is now $394 per person
$394
per person
Mar 21 - Mar 24
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
9.6/10 Exceptional! (89 reviews)
This might be the coolest place I have ever stayed. Rooms are small (used to be a hostel) but spotless as is the rest of the hotel. Great history behind this building. Very comfortable sitting in the great room conversing with others. The peacefulness was in large part due to this being a TV free hotel.

Reviewed on Nov 17, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $1,196, price is now $943 per person
$943
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay.

Reviewed on Jan 10, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $1,495, price is now $1,186 per person
$1,186
per person
Apr 23 - Apr 25
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Kitchen was fully equipped with everything you would need. The rooms were clean and spacious, beautiful building and friendly staff. Parking is what you would expect in a downtown area but was very easy and the attendant was great.

Reviewed on Jan 14, 2026

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was $700, price is now $565 per person
$565
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip flight included
Denver (DEN) to Pittsburgh (PIT)
8.2/10 Very Good! (3,142 reviews)
Rooms need microwaves

Reviewed on Jan 28, 2026

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
$107 nightly
The price is $122 total per night from Feb 12 to Feb 13
$122 total
Feb 12 - Feb 13
Total with taxes and fees
8.2/10 Very Good! (3,383 reviews)
The stay was excellent because of the staff. We were there during a giant snowstorm. The city was basically shut down. Big credit to Cody at the front desk (who I think was stuck there with us) and the others who took care of us when nothing was normal. While standing in the lobby and looking at ...

Reviewed on Jan 27, 2026

Wyndham Grand Pittsburgh Downtown
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 $182 total per night from Feb 8 to Feb 9
$182 total
Feb 8 - Feb 9
Total with taxes and fees
9/10 Wonderful! (1,929 reviews)
Room was very nice. The staff was extremely accommodating. Always stay here when in Pittsburgh.

Reviewed on Jan 22, 2026

Omni William Penn Hotel
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
$105 nightly
The price is $120 total per night from Feb 5 to Feb 6
$120 total
Feb 5 - Feb 6
Total with taxes and fees
8.4/10 Very Good! (1,426 reviews)
Wonderful staff while we were stranded due to snow storm! Served good food and were very attentive!

Reviewed on Jan 26, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,905 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
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Discover the most popular places to visit in Brookline

PNC Park showing a city

PNC Park

4.5/5(780 reviews)

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

PNC Park
University of Pittsburgh in Pittsburgh, PA

University of Pittsburgh

4.5/5(843 reviews)

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
Mario Lemieux statue

PPG Paints Arena

4.5/5(596 reviews)

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

Things to do

Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena

Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena

$106
per adult
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

$67
per adult
Pittsburgh Pirates Baseball Game at PNC Park
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
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.