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.
Microtel Inn & Suites By Wyndham Beaver Falls

Microtel Inn & Suites By Wyndham Beaver Falls

2.5 out of 5
Price was CA $1,348, price is now CA $1,214 per person
CA $1,214
per person
Dec 4 - Dec 11
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)

Hilton Garden Inn Pittsburgh Area Beaver Valley, PA

Hilton Garden Inn Pittsburgh Area Beaver Valley, PA

3 out of 5
Price was CA $1,445, price is now CA $1,298 per person
CA $1,298
per person
Dec 4 - Dec 11
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
9.2/10 Wonderful! (591 reviews)

OYO Hotel North Lima OH - Boardman

OYO Hotel North Lima OH - Boardman

2.5 out of 5
Price was CA $1,396, price is now CA $1,255 per person
CA $1,255
per person
Dec 4 - Dec 11
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
6.6/10 (240 reviews)
Terrible place overall. I would not recommend to anyone.

Reviewed on Oct 19, 2026

Holiday Inn Express & Suites Sharon-Hermitage by IHG

Holiday Inn Express & Suites Sharon-Hermitage by IHG

2.5 out of 5
Price was CA $1,590, price is now CA $1,446 per person
CA $1,446
per person
Jan 1 - Jan 8
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
9.6/10 Exceptional! (753 reviews)
This is the BEST Holiday Inn that we have ever visited. It was very clean and beautifully decorated. The staff was very friendly. The amenities are unbelievable! Free snacks in the evening, and a buffet breakfast bar that was the most expansive I have ever seen in a free breakfast. They thought of every detail - including honey & lemon for my tea! We would definitely stay here again.

Reviewed on Oct 26, 2026

Holiday Inn Express & Suites Monaca - Center Township

Holiday Inn Express & Suites Monaca - Center Township

2.5 out of 5
Price was CA $1,478, price is now CA $1,363 per person
CA $1,363
per person
Jan 8 - Jan 15
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.4/10 Very good! (323 reviews)
This is a nice hotel. I would have liked them to make the. Bed every day. I don’t need sheets every day but it’s treat when travel not th have to make the bed.

Reviewed on Oct 26, 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.

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 $173 per night from Nov 23 to Nov 24
CA $173
CA $197 total
Nov 23 - Nov 24
includes taxes & fees
Wyndham Grand Pittsburgh Downtown
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Nov 15 to Nov 16
CA $157
CA $179 total
Nov 15 - Nov 16
includes taxes & fees
9.4/10 Exceptional! (2,498 reviews)
"I had a wonderful experience staying in this suite! The room was beautiful, comfortable, and well-maintained. Everything was great, and the overall experience made my stay special. The breakfast was also delicious and fresh, which made the experience even better. The only small suggestion I would ..."

Reviewed on Oct 28, 2026

The Landing Hotel at Rivers Casino
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
500 Mansfield Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Nov 8 to Nov 9
CA $142
CA $162 total
Nov 8 - Nov 9
includes taxes & fees
DoubleTree by Hilton Pittsburgh - Green Tree
See all 2,004 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
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Frequently asked questions

How much does a Squirrel Hill vacation package cost?
Our Squirrel Hill vacation packages, which begin from just CA $1,214, 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.

Stay near popular Squirrel Hill attractions

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.
See properties

Things to do

Picture 3 for Activity Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

CA $41
per adult
86% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
This tour is the best tour for sports fans! Big fun guaranteed!

Black & Gold Pittsburgh History Tour for Sports Fans

CA $46
per adult
Black & Gold Pittsburgh History Tour for Sports Fans
Best of the Burgh Walking Tour of Pittsburgh

Best of the Burgh Walking Tour of Pittsburgh

CA $46
per adult
100% of travellers recommend
Best of the Burgh Walking Tour of Pittsburgh
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.