Brentwood Vacation Packages

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Your Brentwood Vacation

From its highlights to its hidden gems, this city is best explored with a Brentwood vacation package. Check out places to stay in Downtown Pittsburgh, which is good for markets, dining and views. You'll want to go sightseeing during your trip to Brentwood. Find time for famous attractions like Acrisure Stadium, University of Pittsburgh and PNC Park. Don't put off your visit to this destination any longer. Your dream Brentwood vacation is a couple of clicks away with Expedia.

Top Brentwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pittsburgh Airport Inn and Suites

Pittsburgh Airport Inn and Suites

2.5 out of 5
Price was CA $1,206, price is now CA $1,183 per person
CA $1,183
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8.4/10 Very good! (1,017 reviews)
Solid breakfast with surprisingly delicious juices.

Reviewed on Nov 6, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,587, price is now CA $1,488 per person
CA $1,488
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)

Hyatt Place at The Hollywood Casino / Pittsburgh - South

Hyatt Place at The Hollywood Casino / Pittsburgh - South

3 out of 5
Price was CA $1,418, price is now CA $1,359 per person
CA $1,359
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8.4/10 Very good! (1,003 reviews)
Great staff member when checking in. Fast and easy. Room was very nice. Lots of room, clean and comfortable. Love that this hotel was connected to the casino without going out in the rain. I would recommend this hotel without any hesitation.

Reviewed on Nov 6, 2026

The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
Oakland
Price was CA $1,494, price is now CA $1,443 per person
CA $1,443
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
9.2/10 Wonderful! (846 reviews)
Johnathan the bellhop went above and beyond to show us everything and gave helpful tips for the area

Reviewed on Nov 2, 2026

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

2.5 out of 5
North Shore
Price was CA $1,374, price is now CA $1,364 per person
CA $1,364
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8.6/10 Excellent! (1,599 reviews)
Great location. Breakfast was very good. Lots to do in the area within walking distance. Hotel was clean, beds were comfy and staff was very friendly and helpful. We would definitely staff here again.

Reviewed on Nov 7, 2026

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Brentwood 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
The price is CA $173 per night from Nov 25 to Nov 26
CA $173
CA $198 total
Nov 25 - Nov 26
includes taxes & fees
8.4/10 Very good! (3,895 reviews)
"The room was a bit outdated but clean"

Reviewed on Nov 7, 2026

Wyndham Grand Pittsburgh Downtown
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
500 Mansfield Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Dec 8 to Dec 9
CA $149
CA $170 total
Dec 8 - Dec 9
includes taxes & fees
8.8/10 Excellent! (1,300 reviews)
"Great location, Great staff. Bathrooms need renovation."

Reviewed on Nov 7, 2026

DoubleTree by Hilton Pittsburgh - Green Tree
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Nov 9 to Nov 10
CA $151
CA $172 total
Nov 9 - Nov 10
includes taxes & fees
9.4/10 Exceptional! (2,533 reviews)
"The stay was alright, in general. Unfortunately the casino ventilation and air control is poor. The non-smoking section is pretty much non-existent. The breakfast section didn’t have much variety but it was okay. Staff were friendly. Location was good."

Reviewed on Nov 7, 2026

The Landing Hotel at Rivers Casino
See all 1,939 properties in Brentwood
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.
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What to do in Brentwood

Picture 3 for Activity Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

CA $41
per adult
86% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
Pittsburgh: Beauty of the Burgh Bike Tour

Pittsburgh: Beauty of the Burgh Bike Tour

CA $83
per adult
94% of travellers recommend
Pittsburgh: Beauty of the Burgh Bike Tour
Make new friends as you learn the exciting history of whiskey in Pittsburgh

Whiskey Rebellion & Prohibition Tour

CA $69
per adult
100% of travellers recommend
Whiskey Rebellion & Prohibition Tour
See all activities in Brentwood

Frequently asked questions

How much does a Brentwood vacation package cost?
You'll find cheap prices from CA $1,183 on Expedia for your Brentwood break. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Brentwood costs.
What are the cheapest months to go to Brentwood?
If you'd like to book a cheap Brentwood vacation package, consider travelling in January, February and March. You'll typically find better prices on flights and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Brentwood?
We recommend planning a Brentwood vacation for a minimum of 2 days. This gives you enough time to check off top attractions including Andy Warhol Museum and Stage AE, and also check out neighbourhoods like Downtown Pittsburgh and Oakland. You could even make time for a day trip or two outside of Brentwood.
How to find the best Brentwood package deals?
Begin your search for a Brentwood package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Brentwood package deal right away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Brentwood escape off to a flying start.
Is it cheaper to book a Brentwood vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still get the flexibility to create a customized Brentwood vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Brentwood?
Secure fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Brentwood getaway.
How to plan a trip to Brentwood?

  1. Choose when to travel: Check your diary and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to vacation in Brentwood.
  2. Set a budget: Consider costs such as flights, food and transportation when calculating how much to save for your trip to Brentwood. Then, pick a hotel that matches your budget, whether that's a low-cost option or a more luxurious retreat.
  3. Decide your trip length: Consider how long you'd like to spend discovering Brentwood. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Brentwood vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.