Squirrel Hill Vacation Packages

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Top Holiday Package Deals in Squirrel Hill

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
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.2/10 Very Good! (1,006 reviews)
Parking. 32.00 is steep when you are paying price for room. Booked thru third party which I didn’t know I did. Tv didn’t work. Called desk. Sent two guys up. First one had no idea what to do. Sent second guy who stated he was housekeeping. Took tv off wall and never came back. My husband fixed t.v. As it sat on counter.

Reviewed on Jul. 13, 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
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.2/10 Very Good! (1,322 reviews)
We stayed at the Joinery Hotel in Pittsburgh and unfortunately, it didn’t live up to expectations. The air conditioning in our room was POOR — it barely worked and left the room feeling stuffy and musty the entire time. The location also wasn’t quite as “downtown” as we expected; it was a bit farther from the main attractions than we expected, so expect to be walking or driving more. We were also really looking forward to the rooftop terrace, but it was closed during our stay with no notice, which was disappointing. Overall, the hotel just didn’t meet the standard I usually associate with Hilton properties. For the price and brand name, I expected a more comfortable and polished experience. On the pulse side we did have really great bartenders and drinks at Millhouse

Reviewed on Jul. 13, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8/10 Very Good! (2,882 reviews)
The customer service was not consistent. While the valet and bell hops were very timely and professional, there was a lack of professionalism at the coffee station in the morning.

Reviewed on Jul. 14, 2025

Placemakr Downtown Pittsburgh

Placemakr Downtown Pittsburgh

4 out of 5
Downtown Pittsburgh
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
7.2/10 Good! (10 reviews)
Practical and accessible

Reviewed on Jul. 12, 2025

Renaissance Pittsburgh Hotel

Renaissance Pittsburgh Hotel

4 out of 5
Downtown Pittsburgh
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
9/10 Wonderful! (1,002 reviews)
Absolutely loved the hotel. The room was very spacious and had a fantastic view. The staff was great. The bar inside the hotel was relaxed and the bartender was awesome. There is so many dining options within walking distance from the hotel. During my stay they was doing the Picklesburgh Festival, and this did not impact my stay at all. It was a great stay, planning to do it again soon.

Reviewed on Jul. 11, 2025

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(187 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

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
The price is CA $170 per night from Jul 16 to Jul 17
CA $170
CA $194 total
Jul 16 - Jul 17
includes taxes & fees
8/10 Very Good! (2,884 reviews)
"Great stay. Location is really convenient."

Reviewed on Jul. 11, 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
The price is CA $196 per night from Jul 28 to Jul 29
CA $196
CA $224 total
Jul 28 - Jul 29
includes taxes & fees
9/10 Wonderful! (1,534 reviews)
"Beautiful property."

Reviewed on Jul. 13, 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
The price is CA $173 per night from Jul 20 to Jul 21
CA $173
CA $198 total
Jul 20 - Jul 21
includes taxes & fees
8.2/10 Very Good! (1,326 reviews)
"Great customer service, friendly front desk agent , he upgraded us, highly recommend"

Reviewed on Jul. 13, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,813 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

Family Vacations

Family Vacations

Frequently asked questions

How much does a Squirrel Hill vacation package cost?
Our Squirrel Hill vacation packages, which begin from just CA $957, are the easiest way to save big. Pick and choose your favorite flights, hotels and rental cars to create your perfect escape.
How do I get a cheap travel package to Squirrel Hill?
Browse and lock in everything in the one place with our Squirrel Hill vacation packages. We have incredible bargains on flights, hotels, tours and more that'll keep your credit card happy and your adventurous spirit busy. And, with more than 550 partner airlines and 1,000,000 hotel options around the globe to select from, you'll have endless opportunities to mix and match as you want.
Where should I stay in Squirrel Hill?
Most who travel to Squirrel Hill include Acrisure Stadium and PNC Park on their to-do lists. Why not go for a hotel as close as possible to these great attractions?
What are the top hotels in Squirrel Hill?
If it's your first time staying in Squirrel Hill, make a reservation at The Mansion At Maple Heights or Pittsburgh Townhome ~ 5 Miles To Market Square. Both hotels offer friendly service and are favorites among many travelers.
How far in advance should I book my Squirrel Hill vacation?
Smart travelers will likely want to reserve their seats as early as possible. You can generally look up international fares on Expedia up to 12 months before your flight. If you're booking at the last minute, there's no need to worry. Budget prices occasionally become available just weeks before departure dates.
What does an Expedia Squirrel Hill travel package include?
That depends on you. You can select from a range of Squirrel Hill bundles, such as a hotel, rental car and flight. You can also book a flight and a hotel, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your dream Squirrel Hill escape looks like, you're sure to save!
What should I know before booking a Squirrel Hill travel package?
Discover deals that match your budget with an Expedia package. Flights, hotels, rental cars --- we've got them all. You'll save loads just by combining your bookings. Whether you're taking off on a ski trip or sipping cocktails on a beach, your dream getaway is just clicks away.
Can I choose my airline with a Squirrel Hill Expedia vacation package?
Yes, so take your pick! We offer more than 550 partner airlines throughout the world, so you can design your Squirrel Hill adventure according to your budget and travel needs.
If I'm not able to travel, can I cancel my Squirrel Hill vacation package?
Whether it's your hotel or flight, you can cancel or alter it. Booked your Squirrel Hill vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings made more than 24 hours ago, you may incur a fee from your airline, hotel or car rental company. For more information, browse our Customer Service Portal. We'll help you every step of the way.

Discover the most popular places to visit in Squirrel Hill

Carnegie Mellon University

Carnegie Mellon University

Walk around the campus of Carnegie Mellon University, a top college in Pittsburgh. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Carnegie Mellon University
PNC Park which includes a city

PNC Park

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

PNC Park
University of Pittsburgh

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

Things to do

Visit beautiful shopping and dining complex in your private tour

Private City Kickstart Tour: Tokyo

CA $185
per adult
100% of travellers recommend
Private City Kickstart Tour: Tokyo
JUST THE TOUR - An open top Double Decker Bus Sightseeing Tour of Pittsburgh.

JUST THE TOUR - Double Decker bus sightseeing tour of Pittsburgh.

CA $62
per adult
94% of travellers recommend
JUST THE TOUR - Double Decker bus sightseeing tour of Pittsburgh.
Happy hour cruiser

2 Hour Private Sightseeing Charter Boat Cruise

CA $527
per traveller
2 Hour Private Sightseeing Charter Boat Cruise
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.