Pleasant Hills Vacations from $194

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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.

The Latest Pleasant Hills vacation packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn Pittsburgh Airport
Hotel Indigo Pittsburgh East Liberty by IHG
Wyndham Grand Pittsburgh Downtown
The Westin Pittsburgh, a Marriott Hotel
Renaissance Pittsburgh Hotel
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Discover the most popular places to visit in Pleasant Hills

What to do in Pleasant Hills

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
$152 nightly
The price is $173 total per night from Aug 27 to Aug 28
$173 total
Aug 27 - Aug 28
Total with taxes and fees
8/10 Very Good! (2,959 reviews)
"Hotel was ok. Staff was nice. Hotel needs to be modernized though."

Reviewed on Aug 22, 2025

Wyndham Grand Pittsburgh Downtown
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
$159 nightly
The price is $182 total per night from Sep 10 to Sep 11
$182 total
Sep 10 - Sep 11
Total with taxes and fees
9/10 Wonderful! (1,613 reviews)
"Everything great, nice people, nice installation"

Reviewed on Aug 23, 2025

Omni William Penn Hotel
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
$121 nightly
The price is $137 total per night from Sep 7 to Sep 8
$137 total
Sep 7 - Sep 8
Total with taxes and fees
8.2/10 Very Good! (1,339 reviews)

Reviewed on Aug 21, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
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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Frequently asked questions

How much does a Pleasant Hills vacation package cost?
Offering great value package deals from $194 on Expedia, you'll be thrilled with how little a vacation to Pleasant Hills costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Pleasant Hills?
November, December and January are great times to look for cheap Pleasant Hills vacation packages. Opting to travel in quieter months means you'll typically find reduced prices on flights and hotels.
How many days is enough for Pleasant Hills?
The ideal duration of your Pleasant Hills vacation depends on what you'd like to see and do. Usually, a few days to a week will give you time to visit all the major attractions and discover some hidden treasures along the way.
How to find the best Pleasant Hills package deals?
Finding a cheap Pleasant Hills package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most pocket-friendly Pleasant Hills package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Pleasant Hills vacation as a package?
You can enjoy significant savings on your next Pleasant Hills getaway by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Pleasant Hills?
If you're planning an impromptu Pleasant Hills trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Pleasant Hills?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Pleasant Hills.
  2. Budget wisely: As well as the cost of your hotel, you'll need to factor in other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Pleasant Hills.
  3. Explore Pleasant Hills using our trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Pleasant Hills. You can also save your favorite locations, collaborate with your group and arrange all your plans in one place.
  4. Decide your trip length: Consider how long you'd like to spend exploring Pleasant Hills. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  5. Combine your airfare and accommodations: Once you've nailed down your travel dates and duration, lock in the perfect Pleasant Hills vacation package for you.
  6. Book any day trips or activities: Now to the fun part — organizing everything you want to see and do. Browse some of the exciting things to do in Pleasant Hills and reserve your tickets early to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Pleasant Hills vacation packages?
Your Pleasant Hills break should be a relaxing escape from your busy life, not a reason for money-related stress. So to give you extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.