Squirrel Hill Vacation Packages 2026 from $508

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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.

Americas Best Value Inn Pittsburgh Airport

$508

per person

Oct 28 - Nov 2

found 15 hours ago

Roundtrip non-stop flight included

Las Vegas (LAS) to Pittsburgh (PIT)

6.6/10 (1,002 reviews)

Stay Pittsburgh

Downtown Pittsburgh

$906

per person

Nov 26 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Pittsburgh (PIT)

8/10 Very Good! (325 reviews)

Apartment was on a very busy street next to a 24 hr store and had a lot of people just standing around on the corner all day and night. Not the safest spot after dark. You could hear everything on the street all night, so hard to fall asleep. Building and hall smelled like weed but the apartment was fine. I texted the number that gave me the code and they said they would check the floor, address the issue and keep me posted. Never heard back from them. No thrills but didn’t expect any given the cost. Parking was supposed to be $25/day with in and out privileges in the assigned parking lot but there was never an attendant there so no in and out and charged $30/day.

Reviewed on Sep 20, 2026

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

$1,011

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Pittsburgh (PIT)

8.6/10 Excellent! (1,004 reviews)

I would highly recommend! We spent our 2nd anniversary there for the Steelers game and when we arrived to our room they were so kind to leave us some goodies and a little note to congratulate us! It was a very clean hotel and room! Staffing very kind! Will be staying again for sure!

Reviewed on Sep 14, 2026

Oakmont Inn

Plum

$723

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

New York (NYC) to Pittsburgh (PIT)

10/10 Exceptional! (38 reviews)

From the minute we arrived to the minute we checked out, an amazing stay, very clean, beds comfortable, convenient location. Great space downstairs for family, gym, and breakfast each morning was wonderful. Will stay here again and recommend to friends and family

Reviewed on Jul 5, 2026

Crowne Plaza Suites Pittsburgh South by IHG

$534

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

New York (NYC) to Pittsburgh (PIT)

8.6/10 Excellent! (1,004 reviews)

Maid service was spotty and there is no safe.

Reviewed on Sep 21, 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

A yellow bridge over a river with a cityscape in the background.

Downtown Pittsburgh

2 out of top 10 points of interest in this area

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.

A yellow bridge over a river, a weeping willow tree, and a modern building with glass windows.

North Shore

2 out of top 10 points of interest in this area

Heinz Field, PNC Park, and The Andy Warhol Museum await in this vibrant area, connected to Downtown Pittsburgh by the iconic Roberto Clemente, Andy Warhol, and Rachel Carson Bridges. Enjoy easy access to two light rail stations.

The Mellon Institute at Carnegie Mellon University with classical columns and a Gothic cathedral in the background.

Oakland

1 out of top 10 points of interest in this area

Academic and healthcare hub, Oakland boasts museums, shopping venues, and diverse dining options along Forbes and Fifth Avenue. Explore historic districts and easily navigate the area via the distinctive city steps and public transportation.

A street with a Starbucks and a plaza with colorful steps.

Strip District

Brimming with specialty shops, unique boutiques, and ethnic food purveyors, the Strip District offers a lively atmosphere with art studios, antique dealers, and the historic St. Stanislaus Kostka Church. Enjoy open-air markets and vibrant nightlife during summer months.

A courtyard with a fountain, brick walls, and trees.

Shadyside

Victorian mansions and modern apartments create a diverse residential atmosphere. Explore upscale stores on Walnut Street, dine at local eateries like Pamela's Diner, and easily walk between the three business corridors. Public transportation is accessible.

Squirrel Hill Hotel Deals

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA

Fully refundableReserve now, pay when you stay

$124 nightly

$141 total

Oct 12 - Oct 13

Total with taxes and fees

8.4/10 Very Good! (3,814 reviews)

"Excellent, clean! I'll be back soon!"

Reviewed on Sep 21, 2026

Pittsburgh Marriott City Center

112 Washington Pl Pittsburgh PA

Fully refundableReserve now, pay when you stay

$152 nightly

$173 total

Oct 16 - Oct 17

Total with taxes and fees

8.2/10 Very Good! (1,320 reviews)

"I have some specific feedback that I’d rather share with management directly."

Reviewed on Sep 21, 2026

The Landing Hotel at Rivers Casino

757 Casino Dr Pittsburgh PA

Fully refundableReserve now, pay when you stay

$149 nightly

$170 total

Oct 21 - Oct 22

Total with taxes and fees

See all 2,030 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.

Stay near popular Squirrel Hill attractions

Temple Sinai

Temple Sinai is just one of the places to see in Pittsburgh, so why not enjoy the other things to explore during your travels? Experience the acclaimed theater scene or attend a sporting event in this vibrant area.

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Pittsburgh Center for the Arts

Enjoy an outing to Pittsburgh Center for the Arts during your stay in Pittsburgh. Stroll along the riverfront or attend a sporting event in this vibrant area.

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Purnell Center for the Arts

Enjoy an outing to Purnell Center for the Arts during your stay in Pittsburgh. Make some time to visit the shops while you're in the area.

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Hunt Institute for Botanical Documentation

You can spend an afternoon studying the exhibits at Hunt Institute for Botanical Documentation in Pittsburgh. Amble around this family-friendly area's riverfront or attend a sporting event.

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Things to do

Pittsburgh: Museum of Illusions Entrance Ticket

$29

per adult

94% of travellers recommend

Make new friends as you learn the exciting history of whiskey in Pittsburgh

Whiskey Rebellion & Prohibition Tour

$49

per adult

100% of travellers recommend

Pittsburgh: Pasta Making Class With Local Chef

$75

per adult

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.

Squirrel Hill Vacations from $508

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Squirrel Hill Vacation

The Latest Squirrel Hill Vacation Packages

Americas Best Value Inn Pittsburgh Airport

Stay Pittsburgh

The Westin Pittsburgh, a Marriott Hotel

Oakmont Inn

Crowne Plaza Suites Pittsburgh South by IHG

Where to stay in Squirrel Hill

Downtown Pittsburgh

North Shore

Oakland

Strip District

Shadyside

Squirrel Hill Hotel Deals

Wyndham Grand Pittsburgh Downtown

Pittsburgh Marriott City Center

The Landing Hotel at Rivers Casino

Stay near popular Squirrel Hill attractions

Temple Sinai

Pittsburgh Center for the Arts

Purnell Center for the Arts

Hunt Institute for Botanical Documentation

Things to do

Pittsburgh: Museum of Illusions Entrance Ticket

Whiskey Rebellion & Prohibition Tour

Pittsburgh: Pasta Making Class With Local Chef