Pleasant Hills Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was CA $872, price is now CA $762 per person
CA $762
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,551 reviews)
Check in could have went better.

Reviewed on Jul 12, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was CA $1,621, price is now CA $1,256 per person
CA $1,256
per person
Sep 12 - Sep 15
found 16 hours ago
Roundtrip flight included
Montreal (YMQ) to Pittsburgh (PIT)
8/10 Very good! (302 reviews)
Affordable

Reviewed on Jul 4, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $1,410, price is now CA $1,240 per person
CA $1,240
per person
Sep 12 - Sep 15
found 16 hours ago
Roundtrip flight included
Montreal (YMQ) to Pittsburgh (PIT)
8.6/10 Excellent! (146 reviews)
If you want to park your car and walk the city, this is the perfect location to do so. It is about a mile from everything. We walked to the Strip, the inclines, the Pirates game and never used our car once.

Reviewed on Jul 12, 2026

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Downtown Pittsburgh
Price was CA $1,575, price is now CA $1,395 per person
CA $1,395
per person
Sep 12 - Sep 15
found 16 hours ago
Roundtrip flight included
Montreal (YMQ) to Pittsburgh (PIT)
8.4/10 Very good! (1,078 reviews)
Shower was Luke warm, toilets didn’t flush right, sink dint drain properly.

Reviewed on Jul 12, 2026

The Atterbury Hotel, Autograph Collection

The Atterbury Hotel, Autograph Collection

4 out of 5
Downtown Pittsburgh
Price was CA $1,007, price is now CA $894 per person
CA $894
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
9/10 Wonderful! (1,004 reviews)
Parking nearby, convenient location for baseball/football games. Modern, clean, parking across the street for reasonable cost. Staff very pleasant and accommodating

Reviewed on Jul 11, 2026

Ready to book your vacation to Pleasant Hills?

 

Choose your dates

Pleasant Hills Hotel Deals

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl Pittsburgh PA
The price is CA $257 per night from Aug 2 to Aug 3
CA $257
CA $293 total
Aug 2 - Aug 3
includes taxes & fees
8.2/10 Very good! (3,643 reviews)
"Sliding bathroom door made a lot of noise and wasn't easy to open or close."

Reviewed on Jul 13, 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 $194 per night from Aug 5 to Aug 6
CA $194
CA $222 total
Aug 5 - Aug 6
includes taxes & fees
9.4/10 Exceptional! (1,972 reviews)
"Room was comfy and clean. Bathroom big, great shower. Didn’t do the breakfast. Great location to go to PNC Park. Walked along the river, or golf cart ride was $5/pp"

Reviewed on Jul 13, 2026

The Landing Hotel at Rivers Casino
Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from Jul 26 to Jul 27
CA $225
CA $257 total
Jul 26 - Jul 27
includes taxes & fees
9/10 Wonderful! (802 reviews)
"Nice service, very clean and adjacent to the Pitt campus."

Reviewed on Jul 12, 2026

Courtyard by Marriott Pittsburgh University Center
See all 1,981 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

What to do in Pleasant Hills

Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

CA $79
per adult
Pittsburgh Pirates Baseball Game at PNC Park
Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

CA $41
per adult
90% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
This tour is the best tour for sports fans! Big fun guaranteed!

Black & Gold Pittsburgh History Tour for Sports Fans

CA $46
per adult
Black & Gold Pittsburgh History Tour for Sports Fans
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 $762 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.

Explore a world of travel with Expedia

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