Squirrel Hill Vacations from $272

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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 Squirrel Hill Vacation

Uncovering all that Squirrel Hill has to offer is a breeze when you book a Squirrel Hill vacation package. Noted for its gift and craft shops and more, this inviting neighborhood is calling your name. Not sure where to go during your trip to Squirrel Hill? Nearby attractions such as University of Pittsburgh, Carnegie Mellon University and Pittsburgh Zoo and PPG Aquarium are great places to start. Whatever your ideal Squirrel Hill vacation looks like, you can make it a reality with Expedia.

The Latest Squirrel Hill Vacation Packages

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 $397, price is now $272 per person
$272
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.4/10 Very Good! (1,385 reviews)
Room was small and crowded. We were put into two different rooms and neither had a working TV.

Reviewed on Jan 5, 2026

Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was $410, price is now $287 per person
$287
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (1,003 reviews)
The room was perfect

Reviewed on Dec 30, 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 $1,316, price is now $963 per person
$963
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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

Hilton Garden Inn Pittsburgh/Southpointe

Hilton Garden Inn Pittsburgh/Southpointe

3 out of 5
Price was $478, price is now $354 per person
$354
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
9/10 Wonderful! (1,001 reviews)
Clean and updated and very friendly teammates!

Reviewed on Jan 1, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $510, price is now $378 per person
$378
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Nice rooms, beautiful building, good value, great location.

Reviewed on Jan 4, 2026

Where to stay in Squirrel Hill

Find the best Squirrel Hill areas and neighborhoods for the activities you enjoy most. Learn more about Squirrel Hill
Downtown Pittsburgh which includes a bridge and a river or creek

Downtown Pittsburgh

2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)

Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.

Find hotels in Downtown Pittsburgh

Squirrel Hill Hotel Deals

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 Jan 25 to Jan 26
$182 total
Jan 25 - Jan 26
Total with taxes and fees
9/10 Wonderful! (1,898 reviews)
Clean room, bed was very comfortable, breakfast very good, close to rail system, courteous staff, efficient check-in and check-out

Reviewed on Jan 5, 2026

Omni William Penn Hotel
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
$108 nightly
The price is $123 total per night from Feb 3 to Feb 4
$123 total
Feb 3 - Feb 4
Total with taxes and fees
8.2/10 Very Good! (3,338 reviews)
Elevators were small and the wait time was long

Reviewed on Jan 8, 2026

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
$129 nightly
The price is $147 total per night from Jan 25 to Jan 26
$147 total
Jan 25 - Jan 26
Total with taxes and fees
8.4/10 Very Good! (1,428 reviews)
Great stay

Reviewed on Jan 5, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,877 properties in Squirrel Hill
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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Squirrel Hill

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

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
Oakland featuring a garden

University of Pittsburgh

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

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

PNC Park

Things to do

Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena

Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena

$97
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 Pittsburgh
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.