Brookline Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Holiday Package Deals in Brookline
Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
CA $813
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Pittsburgh (PIT)
8.4/10 Very good! (3,820 reviews)
Beautiful hotel and a great location. It was expensive. Breakfast was not included. Staff was extremely helpful when the person next to us flooded their room, the hallway, & our room. Moved us to another room that was pretty but impractical. No room for anything in the shower. Very little counter space & the room was much smaller & no room for suitcases. I wish we could have stayed in our first room.
Reviewed on Sep 28, 2026
The Inn on Negley
Shadyside
CA $1,080
per person
Nov 6 - Nov 9
found 11 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Pittsburgh (PIT)
10/10 Exceptional! (224 reviews)
So clean! A beautiful house and an amazing breakfast! Staff were wonderful. Short walk to shops and restaurants. Highly recommended.
Reviewed on Sep 23, 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
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.
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.
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.
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.
Shadyside
Victorian mansions and modern apartments create a diverse residential atmosphere. Explore upscale stores on Walnut Street, dine at local eateries like Pamela's Diner, and easily walk between the three business corridors. Public transportation is accessible.
Brookline Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $175
CA $199 total
Oct 12 - Oct 13
includes taxes & fees
8.4/10 Very good! (3,800 reviews)
"Beautiful hotel and a great location. It was expensive. Breakfast was not included. Staff was extremely helpful when the person next to us flooded their room, the hallway, & our room. Moved us to another room that was pretty but impractical. No room for anything in the shower. Very little counter ..."
Reviewed on Sep 28, 2026
Pittsburgh Marriott City Center
112 Washington Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $215
CA $245 total
Oct 16 - Oct 17
includes taxes & fees
8.2/10 Very good! (1,329 reviews)
"The parking is very expensive"
Reviewed on Sep 27, 2026
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $185
CA $211 total
Oct 6 - Oct 7
includes taxes & fees
9.4/10 Exceptional! (2,369 reviews)
"Great location, room and hotel were clean and comfortable. We had a river view which we enjoyed. Hotel was next door to the football stadium and a short walk to PNC baseball park. On game days golfcarts are available for hire for $5. Science museum is next door. Natl Aviary nearby. The hotel is located ..."
Reviewed on Sep 28, 2026
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.
Frequently asked questions
How much does a Brookline vacation package cost?
Our Brookline vacation packages, which begin at just CA $813, are the easiest way to save big bucks. All you have to do is choose your preferred hotels, flights and rental car to create your dream itinerary.
How do I get a cheap travel package to Brookline?
If you love bargains, bundle your bookings into a Brookline vacation package. Whether you're chasing hotels, flights, rental cars or day tours, you can book everything in one place. You'll have lots of choice at your fingertips too. Expedia has more than 550 airlines and 1,000,000 hotel options worldwide to pick from. Fly with who you prefer, stay wherever you like and save a packet — now that's the perfect vacation!
Where should I stay in Brookline?
Take the hassle out of sightseeing by staying within walking distance of Brookline's big attractions. Acrisure Stadium and PNC Park are two which top many visitors' bucket lists.
What are the top hotels in Brookline?
Pittsburgh Home With Deck And Grill is one of Brookline's most popular properties. Lock in a room here and you'll be able to slumber peacefully knowing you're in capable hands.
How far in advance should I book my Brookline vacation?
While not all airlines advertise ticket prices early, you can normally look up international airfares on Expedia up to a year in advance. This is the time you'll bag some fantastic deals. If you're purchasing tickets last minute, you may still be in luck. Sometimes the lowest prices appear a few weeks prior to departure.
What does an Expedia Brookline travel package include?
Travel packages include rental cars, flights and hotels, but you can combine any of them to create your ideal Brookline escape. You can also add on activities and experiences once you've made your booking. You're in the driver's seat! When you bundle your bookings with Expedia, you'll get access to deals you won't find anywhere else.
What should I know before booking a Brookline travel package?
Whether it's adventure or relaxation you're craving, a Brookline vacation package lets you organize your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Brookline Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You're the boss! We have access to more than 550 partner airlines worldwide, so you have lots of choice when organizing your Brookline escape.
If I'm not able to travel, can I cancel my Brookline vacation package?
Don't worry if you're rethinking your Brookline vacation package — you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We get that life can occasionally throw a spanner in the travel works, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.
Things to do
Pittsburgh: Museum of Illusions Entrance Ticket
CA $41
per adult
86% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
CA $45
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
CA $18
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.