Pleasant Hills Vacation Packages
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- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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- Rest easyPlan, 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.
The Inn on Negley
Shadyside
CA $1,383
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) 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
Ready to book your vacation to Pleasant Hills?
Pleasant Hills 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! (3,795 reviews)
"Overall a great experience. Check in was fast and easy. Rooms were nice. Parking was easy."
Reviewed on Sep 27, 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! (1,327 reviews)
"Buen ambiente y todo que a distancia de 15 minutos caminando."
Reviewed on Sep 26, 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
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.
What to do in Pleasant Hills
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
Frequently asked questions
How much does a Pleasant Hills vacation package cost?
You can snap up a vacation package to this destination from CA $812 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?
- 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.
- 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.
- 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.
- 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.
