Squirrel Hill Vacations from ￥256,994

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The Latest Squirrel Hill 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 ￥309,406, price is now ￥256,994 per person
￥256,994
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Pittsburgh (PIT)
8.2/10 Very Good! (3,476 reviews)
Room was fine, but the doors block no sound, so you won’t hear your neighbors, but you will hear everyone walking down the hallway or doors closing. Hoped to eat in on a Saturday night, but the “restaurant/bar” was a little nook that was very loud and completely off-putting.

Reviewed on Apr 29, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was ￥378,768, price is now ￥328,725 per person
￥328,725
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,002 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
Price was ￥316,798, price is now ￥286,695 per person
￥286,695
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Pittsburgh (PIT)
8.4/10 Very Good! (92 reviews)
Pros: cRoom was clean and nice size. Kitchen had everything we have it at home except for food. Bed was very comfortable. Staff and valet were very helpful. We arrived to town early and were checked in at 1pm which was nice, because we wanted to walk to the NFL draft. Cons: one side of the hotel is next to train tracks, Friday night we counted four trains and could hear the trains loud and clear. We counted 4 trains pass by our room between 11 PM and 3:30 AM, so we didn’t sleep most of the night. The hotel has virtually no amenities, no restaurant, and no free breakfast.

Reviewed on Apr 26, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was ￥291,190, price is now ￥263,563 per person
￥263,563
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Pittsburgh (PIT)
8.4/10 Very Good! (1,476 reviews)
Ive never stayed at a hotel with valet parking before. Parking situations tend to make me anxious and I had no idea what to expect. We pulled up and a guy came right over and talked to us. Asked how long we'd be staying, how soon we would need the car if at all during the stay and all that. Check in was fairly normal as any other place. Fast and easy. We stayed for St. Pats and one of the biggest things we were excited about was utilizing the rooftop to watch the parade and what an amazing experience that was!! Highly recommend! The only thing that I think could've been better (which is really just my own opinion) is better explaining the hold that is placed on your card when you check in, then how the valet parking is deducted from that hold rather than you paying. It was a little confusing when i saw it all on my statement but i did work everything out and it was fine! Definitely plan to come back for another stay

Reviewed on Apr 28, 2026

Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
Price was ￥302,440, price is now ￥279,168 per person
￥279,168
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,668 reviews)
It was Amazing there we loved it loved it !! Would definitely recommend highly

Reviewed on Apr 28, 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

Downtown Pittsburgh

2 out of top 10 points of interest in this area
4.5/5(2,278 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 ￥34,301 per night from May 13 to May 14
￥34,301
￥39,103 total
May 13 - May 14
includes taxes & fees
8.2/10 Very Good! (3,507 reviews)
Great location

Reviewed on Apr 29, 2026

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 ￥41,330 per night from May 10 to May 11
￥41,330
￥47,116 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (1,996 reviews)
👍

Reviewed on Apr 27, 2026

Omni William Penn Hotel
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 ￥19,009 per night from May 10 to May 11
￥19,009
￥21,670 total
May 10 - May 11
includes taxes & fees
9.4/10 Exceptional! (1,659 reviews)
Clean

Reviewed on Apr 29, 2026

The Landing Hotel at Rivers Casino
See all 2,058 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.

Frequently asked questions

How much does a Squirrel Hill vacation package cost?
Our Squirrel Hill vacation packages, which begin from just ￥256,994, 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

4.5/5(531 reviews)

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

Carnegie Mellon University
PNC Park

PNC Park

4.5/5(790 reviews)

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

PNC Park
University of Pittsburgh in Pittsburgh, PA

University of Pittsburgh

4.5/5(856 reviews)

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

Things to do

Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

￥11,005
per adult
Pittsburgh Pirates Baseball Game at PNC Park
Pittsburgh Pirates Home Game Ticket at PNC Park

Pittsburgh Pirates Home Game Ticket at PNC Park

￥3,809
per adult
Pittsburgh Pirates Home Game Ticket at PNC Park
Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

￥4,606
per adult
80% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
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.