Pleasant Hills Vacation Packages

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Your Pleasant Hills Vacation

Say farewell to planning hassles and hello to a Pleasant Hills vacation package. With your travel details organized before you take off, you can focus on discovering every inch of this city, starting with Squirrel Hill South, which is good for cycling, golfing and dining. Be sure to get in some sightseeing during your trip to Pleasant Hills. Century III Mall and South Park Golf Course are some of the major attractions to visit. Whoever you're traveling with and whatever the size of your budget, your dream Pleasant Hills vacation is just a few clicks away with Expedia.

Top Pleasant Hills Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Downtown Pittsburgh
Price was CA $947, price is now CA $800 per person
CA $800
per person
Aug 14 - Aug 16
found 24 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.2/10 Very Good! (1,061 reviews)
Curtis at the front desk was very polite and helpful. He helped with directions around the city and check in was quick.

Reviewed on Jun 3, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was CA $1,142, price is now CA $850 per person
CA $850
per person
Aug 14 - Aug 16
found 24 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8/10 Very Good! (287 reviews)
I loved my stay if I’m ever back in Pittsburgh with another person I’ll definitely book here again

Reviewed on Jun 6, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,181, price is now CA $964 per person
CA $964
per person
Aug 14 - Aug 16
found 24 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,000 reviews)
It’s a nice hotel with friendly staff. I think you should give a discount or free parking for people staying at the hotel. The cost to parks adds up quick.

Reviewed on Apr 10, 2026

TRYP by Wyndham Pittsburgh/Lawrenceville

TRYP by Wyndham Pittsburgh/Lawrenceville

3 out of 5
Lawrenceville
Price was CA $1,058, price is now CA $903 per person
CA $903
per person
Aug 14 - Aug 16
found 24 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,009 reviews)
We enjoyed how clean our room was, our housekeeper replaced towels every day and coffee as we requested, lobby stuff was very helpful and informative of activities and different options for their amenities,

Reviewed on Jun 3, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was CA $929, price is now CA $801 per person
CA $801
per person
Aug 14 - Aug 16
found 24 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.4/10 Very Good! (1,518 reviews)
I havnt slept that good in a while , right when I woke up I lifted the sheets to see what brand mattress and pillows they were. 100 out of 10

Reviewed on Jun 5, 2026

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Pleasant Hills 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 $209 per night from Jun 30 to Jul 1
CA $209
CA $238 total
Jun 30 - Jul 1
includes taxes & fees
8.2/10 Very Good! (3,582 reviews)
"GREAT location! It was well within walking distances to all areas downtown, PNC park, and the beautiful park directly across the street. The river view was well worth the price. Double queen room was a little smaller than typical but plenty of space for my family of 4 (2 adults and 2 children under ..."

Reviewed on Jun 6, 2026

Wyndham Grand Pittsburgh Downtown
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 $180 per night from Jun 18 to Jun 19
CA $180
CA $205 total
Jun 18 - Jun 19
includes taxes & fees
9.4/10 Exceptional! (1,794 reviews)
"Great"

Reviewed on Jun 4, 2026

The Landing Hotel at Rivers Casino
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
The price is CA $270 per night from Jun 14 to Jun 15
CA $270
CA $308 total
Jun 14 - Jun 15
includes taxes & fees
9.2/10 Wonderful! (2,015 reviews)
"Clean room and beautiful hotel"

Reviewed on Jun 6, 2026

Omni William Penn Hotel
See all 1,991 properties in Pleasant Hills
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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Discover the most popular places to visit in Pleasant Hills

Acrisure Stadium

Acrisure Stadium

Giant ketchup bottles tilt onto the scoreboard to celebrate touchdowns in this innovative riverside football arena at the heart of Pittsburgh sports.

Acrisure Stadium
University of Pittsburgh in Pittsburgh, PA

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
PNC Park

PNC Park

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

PNC Park

What to do in Pleasant Hills

Picture 4 for Activity Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

CA $40
per adult
80% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
This tour is the best tour for sports fans! Big fun guaranteed!

New! Black & Gold Sports History Tour for Sports Fans

CA $45
per adult
New! Black & Gold Sports History Tour for Sports Fans
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

CA $18
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
See all activities in Pleasant Hills

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