Cheswick Vacations from $287

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Your Cheswick Vacation

The best way to experience this unique city is with a tailor-made Cheswick vacation package. Base yourself in the neighborhood of Lawrenceville, which is great for nightlife, bars and pubs and dining or choose someplace else — our package deals are all about you. Any trip to Cheswick needs a well-thought-out itinerary. Fill yours with leading attractions like Galleria at Pittsburgh Mills, Shady Side Academy and Harmarville Blade Runners Ice Complex. Stop dreaming and start traveling. Check out the many options on Expedia today and finally put your Cheswick vacation plans into action!

The Latest Cheswick vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Save 100% on your flight
Price was $443, price is now $287 per person
$287
per person
Feb 21 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (1,003 reviews)
OVERALL, WOULD STAY THERE AGAIN. Clean room, great staff. However, No easy parking. Valet is $32...huh? Probably because they have to go far and wide to park the vehicle since there's no dedicated parking lot. I originally asked for a king/pull out couch bed, and we had to be moved to a two-queen room. OMG the "mattress" on the pull-out was flat with the springs poking out. They really need to go thru all the rooms with pull-out couches and replace them. They did move us without extra cost. Breakfast was good.

Reviewed on Dec 28, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $555, price is now $328 per person
$328
per person
Feb 21 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.4/10 Very Good! (1,385 reviews)
Clean and courteous!!! My room was small but perfect for a solo traveler. Bed was EXCELLENT!!! Very nice bathroom.

Reviewed on Dec 28, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,441, price is now $891 per person
$891
per person
Feb 21 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Extremely helpful front desk staff facilitated early check in, allowing us to rest prior to event

Reviewed on Dec 27, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $759, price is now $497 per person
$497
per person
Feb 21 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Rooms were great and the location was perfect!

Reviewed on Dec 27, 2025

DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
Save 100% on your flight
Price was $437, price is now $297 per person
$297
per person
Feb 21 - Feb 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (1,004 reviews)
Great place and awesome breakfast!

Reviewed on Dec 23, 2025

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Discover the most popular places to visit in Cheswick

Oakland featuring a garden

University of Pittsburgh

4.5/5(843 reviews)

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 showing a city

PNC Park

4.5/5(780 reviews)

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

PNC Park
The Gates Hillman Center is a unique building that houses the computer science program and research. I love how outside the box the building is #StunningStructures

Carnegie Mellon University

4.5/5(520 reviews)

Take a campus tour or just explore the area of Carnegie Mellon University, during your trip to Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

Carnegie Mellon University

What to do in Cheswick

Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena

Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena

$102
per adult
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

$13
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
Pittsburgh: Beauty of the Burgh Bike Tour

Pittsburgh: Beauty of the Burgh Bike Tour

$59
per adult
94% of travellers recommend
Pittsburgh: Beauty of the Burgh Bike Tour
See all activities in Cheswick

Cheswick 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
$128 nightly
The price is $146 total per night from Dec 29 to Dec 30
$146 total
Dec 29 - Dec 30
Total with taxes and fees
8.2/10 Very Good! (3,302 reviews)
It was a beautiful place to stay with great view of the park and rivers. Room was nice but lacked a coffee maker and microwave which was disappointing and quite shocking, to be honest. The staff were very nice and helpful, especially the bellman and valet drivers. Being unfamiliar with the city we ...

Reviewed on Dec 26, 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 $181 total per night from Jan 4 to Jan 5
$181 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9/10 Wonderful! (1,859 reviews)
Beautiful

Reviewed on Dec 25, 2025

Omni William Penn Hotel
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
112 Washington Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $136 total per night from Dec 30 to Dec 31
$136 total
Dec 30 - Dec 31
Total with taxes and fees
8/10 Very Good! (1,072 reviews)
No soap

Reviewed on Dec 24, 2025

Pittsburgh Marriott City Center
See all 1,883 properties in Cheswick
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.

Find the Best Cheswick Vacation Packages

Cheswick Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Pittsburgh Intl. Airport (PIT)
Population
1,750
Top Sights
Pittsburgh Zoo and PPG Aquarium, Kennywood and Sandcastle Water Park

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Frequently asked questions

How much does a Cheswick vacation package cost?
You'll find cheap prices from $287 on Expedia for your Cheswick escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Cheswick costs.
What are the cheapest months to go to Cheswick?
November, December and January are the best times to search for cheap Cheswick vacation packages. Traveling in quieter periods means you can generally find better prices on accommodations and flights.
How many days is enough for Cheswick?
With a well-organized schedule, you can easily visit the main Cheswick sights in a few days. But if you'd like to explore off the beaten track or go on day tours, think about booking your Cheswick vacation for longer.
How to find the best Cheswick package deals?
Finding a cheap Cheswick package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most affordable Cheswick package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Cheswick vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations separately. Better still, you can customize your Cheswick escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Cheswick?
If you're considering a spontaneous Cheswick vacation, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Cheswick vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Cheswick vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.