Shadyside Holidays

Photo by Hayley Gallagher

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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 Benedum Center or Heinz Hall 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

Mansions on Fifth Hotel

Mansions on Fifth Hotel

4 out of 5
5105 Fifth Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (999 reviews)
Beautifully restored historic buildings. Very convenient to Oakland area of Pittsburgh. Off-street parking, very safe neighborhood.

Reviewed on 1 Jan 2026

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Mansions on Fifth Hotel
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 €156 per night from 23 Jan to 24 Jan
€156
23 Jan - 24 Jan
includes taxes & fees
9/10 Wonderful! (1,914 reviews)
Food at the restaurants was awesome. The staff was amazing and the bed and view were comfortable and inviting.

Reviewed on 11 Jan 2026

Omni William Penn Hotel
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 €106 per night from 3 Feb to 4 Feb
€106
3 Feb - 4 Feb
includes taxes & fees
8.2/10 Very Good! (3,331 reviews)
Friendly staff. Convenient to stadiums. Accommodating to our needs and expectations

Reviewed on 6 Jan 2026

Wyndham Grand Pittsburgh Downtown
See all 1,880 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 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 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.

Things to do

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

€11
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
Pittsburgh: Beauty of the Burgh Bike Tour

Pittsburgh: Beauty of the Burgh Bike Tour

€50
per adult
94% of travellers recommend
Pittsburgh: Beauty of the Burgh Bike Tour
Make new friends as you learn the exciting history of whiskey in Pittsburgh

Whiskey Rebellion & Prohibition Tour

€38
per adult
Whiskey Rebellion & Prohibition Tour
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.