Whitaker Vacations from $459

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Your Whitaker Vacation

When a fun city getaway is calling, answer it with a Whitaker vacation package. The neighborhood of Squirrel Hill South, which is good for cycling, golfing and dining, makes an awesome base for your adventures. The Waterfront, Sandcastle Water Park and Carnegie Museum and Library are just some of the sights you'll want to see during your trip to Whitaker. Expedia is here to help you escape your daily routine. Tailor your vacation to Whitaker to suit your travel style, whatever that may look like.

The Latest Whitaker vacation packages

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 $688, price is now $459 per person
$459
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
8.2/10 Very Good! (3,459 reviews)
Did not eat there Bar not inviting Room clean Parking situation a mess and expensive Disappointed that window had screen put over for an event and was not able to enjoy river view which I had paid more for. Not offered any discount when explained change In room coffee service was not complete with creamer etc..

Reviewed on Apr 13, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $1,309, price is now $875 per person
$875
per person
May 22 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
It’s a nice hotel with friendly staff. I think you should give a discount or free parking for people staying at the hotel. The cost to parks adds up quick.

Reviewed on Apr 10, 2026

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 $985, price is now $705 per person
$705
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
8.4/10 Very Good! (87 reviews)
Walking distance to train and bus transportation. Walking distance to the Strip District. Kitchen was clean and well equipped. Room was quiet, even tho there was a wedding taking place in the hotel. It is a very lovely restored building. Staff was friendly and helpful.

Reviewed on Apr 16, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $790, price is now $572 per person
$572
per person
May 22 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (255 reviews)
Great location, just a couple of blocks from the river, and restaurants literally next door and others close. Keyless entry, management is very available and pro-active. Will be staying again. Thank you!

Reviewed on Apr 14, 2026

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 $1,222, price is now $895 per person
$895
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
8.4/10 Very Good! (1,471 reviews)
A beautiful hotel with great views. The staff was attentive and everything was very clean. Great stay and convenient location.

Reviewed on Apr 15, 2026

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Discover the most popular places to visit in Whitaker

PNC Park

PNC Park

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

PNC Park
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
University of Pittsburgh in Pittsburgh, PA

University of Pittsburgh

Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

University of Pittsburgh

What to do in Whitaker

Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

$29
per adult
80% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
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 Whitaker

Whitaker 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
$149 nightly
The price is $170 total per night from Apr 21 to Apr 22
$170 total
Apr 21 - Apr 22
Total with taxes and fees
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
$117 nightly
The price is $134 total per night from Apr 27 to Apr 28
$134 total
Apr 27 - Apr 28
Total with taxes and fees
8.4/10 Very Good! (1,475 reviews)
A beautiful hotel with great views. The staff was attentive and everything was very clean. Great stay and convenient location.

Reviewed on Apr 15, 2026

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
$187 nightly
The price is $213 total per night from Apr 30 to May 1
$213 total
Apr 30 - May 1
Total with taxes and fees
9.2/10 Wonderful! (1,988 reviews)
People were great

Reviewed on Apr 14, 2026

Omni William Penn Hotel
See all 1,978 properties in Whitaker
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 Whitaker Vacation Packages

Whitaker Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Pittsburgh Intl. Airport (PIT)
Population
1,250
Top Sights
Sandcastle Water Park, Carnegie Museum and Library and Bulgarian Macedonian National Educational and Cultural Center

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Frequently asked questions

How much does a Whitaker vacation package cost?
You'll find cheap prices from $459 on Expedia for your Whitaker getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Whitaker costs.
What are the cheapest months to go to Whitaker?
If you're looking to score a cheap Whitaker vacation package, consider visiting in June, September and October. You're likely to find lower rates on hotels and flights during these months — ideal for budget-conscious travelers.
How many days is enough for Whitaker?
Typically, a handful of days is enough to visit the major sights during your Whitaker vacation. However, if you want to have some time to kick back or go on day tours, consider extending your trip.
How to find the best Whitaker package deals?
Bagging a cheap Whitaker package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Whitaker 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 generally lower.
Is it cheaper to book a Whitaker vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Whitaker vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Whitaker?
Secure incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Whitaker trip.
Does Expedia offer Book Now, Pay Later Whitaker vacation packages?
Your Whitaker trip should be a relaxing escape from your busy life, not a source of money worries. So to give you that extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

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.