Shadyside Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 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
Price found within the past 48 hours. Click for updated prices.
  • Jul 2 - Jul 13

    Stay Pittsburgh + Flight

    Downtown Pittsburgh
    11 nights
    2.0 star property
    8.0/10 - Very Good (282 reviews)
    "It is spacious rooms with dining and living room with nice couches. It is in downtown Pittsburg but quite at night. I liked very much and will visit again in the future"
    Reviewed May 16, 2026
    Roundtrip Tokyo (HND) - Pittsburgh (PIT)
    HND - PIT1 stop PIT - NRT1 stop
    ¥575,809
    ¥433,583
    per traveler
    found 12 hours ago
    Stay Pittsburgh
  • Jul 3 - Jul 13

    Fairmont Pittsburgh + Flight

    Downtown Pittsburgh
    10 nights
    4.5 star property
    8.8/10 - Excellent (1,001 reviews)
    "The room and amenities were excellent but the mattress was worn out had a large depression on one side."
    Reviewed May 14, 2026
    Roundtrip Tokyo (HND) - Pittsburgh (PIT)
    HND - PIT1 stop PIT - NRT1 stop
    ¥788,207
    ¥630,563
    per traveler
    found 12 hours ago
    Fairmont Pittsburgh
  • Jul 2 - Jul 13

    Pittsburgh Marriott City Center + Flight

    Downtown Pittsburgh
    11 nights
    3.5 star property
    8.2/10 - Very Good (1,222 reviews)
    "This was a good property. It was in close proximity to Downtown Pittsburgh. The food at the bar (dinner) was ok. The only downside of this trip is that if you want a hot shower in the morning, get up early because by 8 am, all I had was cold water!!"
    Reviewed May 18, 2026
    Roundtrip Tokyo (HND) - Pittsburgh (PIT)
    HND - PIT1 stop PIT - NRT1 stop
    ¥581,415
    ¥483,788
    per traveler
    found 12 hours ago
    Pittsburgh Marriott City Center
  • Jul 2 - Jul 13

    2bedroom 2bathroom Apt Downtown Walk Anywhere + Flight

    Downtown Pittsburgh
    11 nights
    2.0 star property
    Roundtrip Tokyo (HND) - Pittsburgh (PIT)
    HND - PIT1 stop PIT - NRT1 stop
    ¥610,213
    ¥511,030
    per traveler
    found 12 hours ago
    2bedroom 2bathroom Apt Downtown Walk Anywhere
  • Jul 2 - Jul 13

    2 Bedroom 2 Bathroom The Heart of Pittsburgh + Flight

    Downtown Pittsburgh
    11 nights
    2.0 star property
    Roundtrip Tokyo (HND) - Pittsburgh (PIT)
    HND - PIT1 stop PIT - NRT1 stop
    ¥606,672
    ¥508,510
    per traveler
    found 12 hours ago
    2 Bedroom 2 Bathroom The Heart of Pittsburgh

Where to stay in Shadyside

Find the best Shadyside areas and neighborhoods for the activities you enjoy most. Learn more about Shadyside

Shadyside 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 ¥24,388 per night from Jun 19 to Jun 20
¥24,388
¥27,803 total
Jun 19 - Jun 20
includes taxes & fees
8.2/10 Very Good! (3,540 reviews)
"Perfect all around"

Reviewed on May 18, 2026

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 ¥22,729 per night from May 25 to May 26
¥22,729
¥25,912 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (1,729 reviews)
"Beautiful stay"

Reviewed on May 18, 2026

The Landing Hotel at Rivers Casino
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 ¥30,020 per night from May 24 to May 25
¥30,020
¥34,224 total
May 24 - May 25
includes taxes & fees
9.2/10 Wonderful! (2,002 reviews)
"Stay was great. One complaint was before booking we called and confirmed that room service was available but after arrival learned only for breakfast."

Reviewed on May 18, 2026

Omni William Penn Hotel
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 Shadyside vacation package cost?
From just . Yes, you read that correctly. Our Shadyside vacation packages are the quickest way to make your dollars go much further. Combine your favorite hotels, flights and car rentals and explore this lively destination.
How do I get a cheap travel package to Shadyside?
Booking a Shadyside vacation package with Expedia is a great way to save. We have access to more than 550 partner airlines and 1,000,000 hotels across the globe. With such a broad range to pick from, you'll have no hassles creating your ideal escape.
Where should I stay in Shadyside?
Make sightseeing a breeze by staying someplace just a stone's throw away from Shadyside's biggest attractions. Acrisure Stadium and PNC Park are two traveler favorites.
What are the top hotels in Shadyside?
If it's your very first time in Shadyside, reserve a room at The Inn On Negley or Mansions on Fifth Hotel. Both hotels offer friendly service and are favorites among many savvy travelers.
How far in advance should I book my Shadyside vacation?
It can be tricky to know exactly when the best time is to book your Shadyside vacation. But typically the earlier you book, the better the prices. Sometimes, you can reserve your flights and hotels up to a year before departure. If you're eager to escape on a last-minute getaway, no need to worry! There are terrific bargains advertised on Expedia every day.
What does an Expedia Shadyside travel package include?
Flights, car rentals and hotels — we connect you to the best deals. All you'll have to do is pick and choose your favorite combination. After you've made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it easy to put together an unforgettable Shadyside trip.
What should I know before booking a Shadyside travel package?
You can save big by bundling your hotels, airfares and rental cars. Once you've made your booking, add on fun stuff like tours and activities. Your next awesome vacation is only a few clicks away.
Can I choose my airline with a Shadyside Expedia vacation package?
Yes, you're in charge. We offer more than 550 airlines worldwide, so you can tailor your Shadyside escape according to your travel preferences.
If I'm not able to travel, can I cancel my Shadyside vacation package?
We totally get that life can throw you the odd curveball. If you've booked a Shadyside vacation package and have to cancel or amend it, we can help. We suggest having a look at our Customer Service Portal first for information. But in general, if you've booked your package in the last 24 hours, you may be able to amend or cancel your itinerary at no cost. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.

Discover the most popular places to visit in Shadyside

Things to do

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