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.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was CA $1,429, price is now CA $1,015 per person
CA $1,015
per person
Oct 10 - Oct 13
found 12 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8/10 Very Good! (2,979 reviews)
Great price so close to Acrisure for a football game. Clean and well taken care of

Reviewed on Aug. 21, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $2,124, price is now CA $1,436 per person
CA $1,436
per person
Oct 11 - Oct 14
found 5 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
7.6/10 Good! (12 reviews)
The people at the service desk were fine. Some were helpful and some were not.

Reviewed on Aug. 19, 2025

Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was CA $1,852, price is now CA $1,302 per person
CA $1,302
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.2/10 Very Good! (1,006 reviews)
Good location, friendly staff, spacious bathroom.

Reviewed on Aug. 18, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $2,000, price is now CA $1,430 per person
CA $1,430
per person
Oct 10 - Oct 14
found 5 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.6/10 Excellent! (1,002 reviews)
The property was great the and the sfaff were awesome.

Reviewed on Aug. 17, 2025

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Price was CA $2,731, price is now CA $2,023 per person
CA $2,023
per person
Oct 10 - Oct 13
found 12 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.8/10 Excellent! (1,002 reviews)
Everything was great

Reviewed on Aug. 12, 2025

Ready to book your vacation to Pleasant Hills?

 

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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 $223 per night from Aug 28 to Aug 29
CA $223
CA $255 total
Aug 28 - Aug 29
includes taxes & fees
8/10 Very Good! (2,990 reviews)
"It was my first experience being there, and it was great! I will definitely go back if I’m in the area!"

Reviewed on Aug. 17, 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
The price is CA $161 per night from Sep 3 to Sep 4
CA $161
CA $188 total
Sep 3 - Sep 4
includes taxes & fees
8.2/10 Very Good! (1,345 reviews)
"Perfect place to stay for what we were there for baseball game"

Reviewed on Aug. 18, 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
The price is CA $199 per night from Sep 3 to Sep 4
CA $199
CA $226 total
Sep 3 - Sep 4
includes taxes & fees
9/10 Wonderful! (1,602 reviews)
"Beautiful rooms and facilities. Staff are extremely friendly and welcoming."

Reviewed on Aug. 20, 2025

Omni William Penn Hotel
See all 1,729 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Pleasant Hills

PNC Park which includes a city

PNC Park

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

PNC Park
University of Pittsburgh

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
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

What to do in Pleasant Hills

Pittsburgh, PA: Sandcastle Waterpark Entry Ticket

Pittsburgh, PA: Sandcastle Waterpark Entry Ticket

CA $43
per adult
Pittsburgh, PA: Sandcastle Waterpark Entry Ticket
Visit beautiful shopping and dining complex in your private tour

Private City Kickstart Tour: Tokyo

CA $186
per adult
100% of travellers recommend
Private City Kickstart Tour: Tokyo
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

Frequently asked questions

How much does a Pleasant Hills vacation package cost?
You can snap up a vacation package to this destination from CA $1,015 on Expedia. But how much your vacation to Pleasant Hills costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Pleasant Hills?
To pick up cheap Pleasant Hills vacation packages, plan your getaway outside of busy periods such as public holidays. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Pleasant Hills?
Usually, a handful of days is enough to visit the top sights during your Pleasant Hills vacation. But if you'd like to have more time to rest or go on day tours, think about extending your itinerary.
How to find the best Pleasant Hills package deals?
Begin your search for a Pleasant Hills package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Pleasant Hills package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Pleasant Hills adventure off to a flying start.
Is it cheaper to book a Pleasant Hills vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations individually. Better still, you can customize your Pleasant Hills getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Pleasant Hills?
If you're considering a spontaneous Pleasant Hills trip, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Pleasant Hills?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Pleasant Hills.
  2. Set your budget: Consider expenses such as flights, food and transportation when calculating how much to save for your trip to Pleasant Hills. Then, choose a hotel that works with your budget, whether that's a wallet-friendly option or a deluxe getaway.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Pleasant Hills. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Combine your accommodations and airfare: After you've settled on your dates and duration, lock in the ideal Pleasant Hills vacation package for you.

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