Shadyside Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Hayley Gallagher

Where to stay in Shadyside

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

2 out of top 10 points of interest in this area
4.5/5(15 area reviews)

Abundant dining options, interesting museums and live music are just a few top things to explore in Downtown Pittsburgh. A visit to PPG Paints Arena or Ohio River Valley might round out your trip, and you can jump aboard the metro at Wood Street Station or Steel Plaza Station to get around town.

Find hotels in Downtown Pittsburgh

Top hotels in Shadyside

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 2.719.320 ₫ per night from 16 Dec to 17 Dec
2.719.320 ₫
3.100.025 ₫ total
16 Dec - 17 Dec
includes taxes & fees
8/10 Very Good! (3,134 reviews)
Great location. Clean, friendly, quiet room. Starbucks in the lobby.

Reviewed on 13 Nov 2025

Wyndham Grand Pittsburgh Downtown
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 3.003.373 ₫ per night from 23 Nov to 24 Nov
3.003.373 ₫
3.492.356 ₫ total
23 Nov - 24 Nov
includes taxes & fees
8.4/10 Very Good! (1,384 reviews)
Loved the lobby and unique decor. Server at Millhouse was exceptional.

Reviewed on 11 Nov 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
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 4.405.931 ₫ per night from 16 Nov to 17 Nov
4.405.931 ₫
5.022.761 ₫ total
16 Nov - 17 Nov
includes taxes & fees
9/10 Wonderful! (1,753 reviews)
Clean room good was Amazing!

Reviewed on 5 Nov 2025

Omni William Penn Hotel
See all 1,829 properties in Shadyside
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 holiday package cost?
From just . Yes, you read that correctly. Our Shadyside holiday packages are the quickest way to make your dollars go much further. Combine your favourite hotels, flights and car rentals and explore this lively destination.
How do I get a cheap travel package to Shadyside?
Booking a Shadyside holiday package with Expedia is a great way to save. We have access to more than 550 partner airlines and 1null000null000 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 traveller favourites.
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 favourites among many savvy travellers.
How far in advance should I book my Shadyside holiday?
It can be tricky to know exactly when the best time is to book your Shadyside holiday. 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 favourite 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 holiday is only a few clicks away.
Can I choose my airline with a Shadyside Expedia holiday 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 holiday package?
We totally get that life can throw you the odd curveball. If you've booked a Shadyside holiday 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.

Popular places to visit

Acrisure Stadium

Acrisure Stadium

Catch an event at Acrisure Stadium during your trip to Pittsburgh. Stroll along the riverfront or attend a sporting event in the area.

Acrisure Stadium
PPG Paints Arena

PPG Paints Arena

Catch an event at PPG Paints Arena during your trip to Pittsburgh. Experience the acclaimed theatre scene or attend a sporting event in this vibrant area.

PPG Paints Arena
PNC Park featuring a city

PNC Park

Catch an event at PNC Park during your trip to Pittsburgh. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.

PNC Park