Title: Book the Best Shadyside LUXURY Hotels - Upscale Hotels in Shadyside, Pittsburgh | Expedia.ca [Shadyside Travel Guide](https://expedia.ca/Pittsburgh-Shadyside.dx6156339)[Vacation Rentals in Pittsburgh](https://expedia.ca/Pittsburgh-Vacation-Rentals.d601717.Travel-Guide-VacationRentals)[Flights to Pittsburgh](https://expedia.ca/Cheap-Flights-To-Pittsburgh.d601717.Travel-Guide-Flights)[Things to do in Pittsburgh](https://expedia.ca/Things-To-Do-In-Pittsburgh.d601717.Travel-Guide-Activities)[Shadyside Car Rentals](https://expedia.ca/Car-Rentals-In-Shadyside.d6156339.Car-Rental-Guide)[Shadyside Vacations](https://expedia.ca/Shadyside.d6156339.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/c39807358559baee6b6d0f04b71891a6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Hayley Gallagher # Find Luxury Hotels in Shadyside, Pittsburgh ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Shadyside Luxury Hotels Tonight [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=6156339&startDate=2025-10-15&endDate=2025-10-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=6156339&startDate=2025-10-16&endDate=2025-10-17&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6156339&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6156339&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Shadyside Luxury Hotels ![Interior](https://images.trvl-media.com/lodging/9000000/8040000/8035100/8035042/6d3246bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8040000/8035100/8035042/2df82a1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed (Fifth Avenue House)](https://images.trvl-media.com/lodging/9000000/8040000/8035100/8035042/17d03475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/9000000/8040000/8035100/8035042/98e3a2c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mansions on Fifth Hotel Shadyside 8.8/10 Excellent (1002) "This was the second time that I have stayed at the Mansions. It really is a charming and elegant home turned hotel. The rooms are clean. The staff are nice. And the parking is a great bonus. I look forward to my next trip to Pittsburgh!" CA $252 CA $287 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Pittsburgh-Hotels-Mansions-On-Fifth-Hotel.h8035042.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30®ionId=6156339&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Shadyside ### Shadysideand its attractions for luxury travelers In the heart of Shadyside, luxury travellers will find a delightful blend of upscale boutiques and cultural experiences. Start your day with a visit to the renowned Shadyside Farmers Market, where local vendors offer fresh produce and artisanal goods, perfect for a leisurely morning stroll. Art enthusiasts can immerse themselves in the vibrant local scene at the nearby Andy Warhol Museum, which highlights the iconic pop artist's life and works, making for an inspiring afternoon. For relaxation, the lush expanses of Frick Park provide a serene escape, ideal for a family picnic or a casual walk surrounded by nature. Dining in Shadyside is a treat, with establishments like the elegant Butcher and the Rye, known for its innovative American cuisine and extensive whiskey selection, ensuring a memorable culinary experience. After a day of exploration, retreat to one of the luxurious hotels in the area, where you can expect personalised service and exquisite amenities. Picture unwinding in a plush suite with stunning views, a spa-like bathroom, and perhaps a complimentary bottle of wine waiting for you—perfect after a day of adventure. Shadyside's blend of culture, dining, and nature ensures that every moment of your stay is filled with quality and comfort, making it an attractive choice for discerning travellers. ### Find the best luxury hotels and resorts in Shadyside For those seeking an opulent retreat in Shadyside, Pittsburgh, these two hotels offer exceptional luxury amenities and exquisite service, ensuring a memorable stay. [The Inn on Negley](https://www.expedia.ca/Pittsburgh-Hotels-The-Inn-On-Negley.h1154383.Hotel-Information) - **Why it's great for a luxury retreat:** The Inn on Negley stands as a pinnacle of luxury with an outstanding guest review rating of 10.0, making it an ideal choice for those looking for an intimate and exquisite experience. This Victorian hotel features premium bedding and bathrobes, complemented by designer toiletries that elevate the overall comfort. Guests can indulge in couples dining with a private chef, along with personalised champagne service, creating a truly romantic atmosphere. - **Other amenities:** Additional offerings include a serene garden and a terrace for peaceful outdoor relaxation. Guests enjoy complimentary breakfast options and the chance to unwind with onsite spa services, including Swedish and deep tissue massages. With early check-in and late check-out options, as well as in-room mini-refrigerators, The Inn on Negley ensures a luxurious and accommodating stay. - **Neighborhood:** Shadyside - **Nearby attractions:** UPMC Shadyside - 1 km, Bakery Square - 1.8 km, Carnegie Mellon University - 2.3 km [Mansions on Fifth Hotel](https://www.expedia.ca/Pittsburgh-Hotels-Mansions-On-Fifth-Hotel.h8035042.Hotel-Information) - **Why it's great for a luxury retreat:** The Mansions on Fifth Hotel is a stunning representation of luxury and elegance, a remarkable guest review rating of 8.8. This Edwardian hotel offers a unique charm, with premium bedding, designer toiletries, and plush bathrobes that create a sophisticated atmosphere for travelers. The attentive concierge service is always on hand to assist with personalised requests, ensuring that every aspect of your stay is catered to perfection. - **Other amenities:** Guests can enjoy a range of additional features, including 24-hour fitness facilities for those looking to maintain their workout routine. The hotel also offers hydromassage showerheads for a touch of relaxation, as well as off-street parking for added convenience. With beautiful terraces and daily housekeeping, every detail is covered to enhance comfort and luxury throughout your visit. - **Neighborhood:** Shadyside - **Nearby attractions:** Carnegie Museum of Natural History - 1.4 km, UPMC Shadyside - 1.5 km, Carnegie Mellon University - 1.1 km ## Top Shadyside Hotel Reviews ![Drury Plaza Hotel Pittsburgh Downtown](//images.trvl-media.com/lodging/16000000/15180000/15178500/15178439/9183e33f_y.jpg) ### Drury Plaza Hotel Pittsburgh Downtown 10/10 Excellent "Nice hotel with friendly staff. I enjoyed the free breakfasts and dinners. " [](https://expedia.ca/Pittsburgh-Hotels-Drury-Plaza-Hotel-Pittsburgh-Downtown.h15178439.Hotel-Information) ![Hyatt Regency Pittsburgh International Airport](//images.trvl-media.com/lodging/1000000/470000/464100/464013/1caa2404_y.jpg) ### Hyatt Regency Pittsburgh International Airport 10/10 Excellent "Easy walk from airport so we saved on rental car for 1 day. Nice rooms and friendly staff. " [](https://expedia.ca/Pittsburgh-Hotels-Hyatt-Regency-Pittsburgh-International-Airport.h464013.Hotel-Information) ![DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown](//images.trvl-media.com/lodging/1000000/10000/6200/6149/4d6098b6_y.jpg) ### DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown 10/10 Excellent "Great hotel" [](https://expedia.ca/Pittsburgh-Hotels-DoubleTree-By-Hilton-Hotel-Suites-Pittsburgh-Downtown.h6149.Hotel-Information) ![Sheraton Pittsburgh Hotel at Station Square](//images.trvl-media.com/lodging/1000000/30000/20400/20319/ae616b8b_y.jpg) ### Sheraton Pittsburgh Hotel at Station Square 10/10 Excellent "Nice location parking little hard lot always full" [](https://expedia.ca/Pittsburgh-Hotels-Sheraton-Pittsburgh-Hotel-At-Station-Square.h20319.Hotel-Information) ![Cambria Hotel Pittsburgh - Downtown](//images.trvl-media.com/lodging/4000000/3910000/3907800/3907735/7ebc27be_y.jpg) ### Cambria Hotel Pittsburgh - Downtown 10/10 Excellent "Shower faucet was leaking, but otherwise absolutely incredible " [](https://expedia.ca/Pittsburgh-Hotels-Cambria-Hotel-Pittsburgh-Downtown.h3907735.Hotel-Information) ![Hilton Garden Inn Pittsburgh University Place](//images.trvl-media.com/lodging/1000000/120000/119000/118998/6c759b6f_y.jpg) ### Hilton Garden Inn Pittsburgh University Place 10/10 Excellent "Very safe place," [](https://expedia.ca/Pittsburgh-Hotels-Hilton-Garden-Inn-Pittsburgh-University-Place.h118998.Hotel-Information) ![Wyndham Grand Pittsburgh Downtown](//images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a_y.jpg) ### Wyndham Grand Pittsburgh Downtown 10/10 Excellent "Clean room and friendly staff " [](https://expedia.ca/Pittsburgh-Hotels-Wyndham-Grand-Pittsburgh-Downtown.h25509.Hotel-Information) ![DoubleTree by Hilton Pittsburgh - Green Tree](//images.trvl-media.com/lodging/1000000/20000/12400/12343/ea79878f_y.jpg) ### DoubleTree by Hilton Pittsburgh - Green Tree 10/10 Excellent "Everything was great" [](https://expedia.ca/Pittsburgh-Hotels-Doubletree-By-Hilton-Pittsburgh-Greentree.h12343.Hotel-Information) ![Omni William Penn Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2998/c923b3f2_y.jpg) ### Omni William Penn Hotel 10/10 Excellent "We were very happy with our stay, room was large, elevators quick. Easy access to everything" [](https://expedia.ca/Pittsburgh-Hotels-Omni-William-Penn-Hotel.h2998.Hotel-Information) ## Frequently asked questions ### Are you looking for a luxury hotel for your stay in Shadyside? > Use Expedia to arrange your flight to Pittsburgh Intl. Airport (PIT) airport or Latrobe, PA (LBE-Arnold Palmer Regional) airport, and then select from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a vacation, so we make it easy to find what you'd like to make your stay relaxing and comfortable. If you want an upscale hotel that has a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Shadyside offers. During your visit, you might want to enjoy the restaurants and bars which Shadyside is known for. ### What's there to see and do in Shadyside? > Experience all that Shadyside has to offer when you visit Walnut Street, Gallerie CHIZ, and Mellon Park Tennis Center. 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[Flights to Pittsburgh](https://www.expedia.ca/Cheap-Flights-To-Pittsburgh.d601717.Travel-Guide-Flights) - [Carnegie Mellon University](https://www.expedia.ca/Carnegie-Mellon-University-Squirrel-Hill.d6090503.Vacation-Attraction) - [Carnegie Museum of Art](https://www.expedia.ca/Carnegie-Museum-Of-Art-Oakland.d6078685.Vacation-Attraction) - [Carnegie Museum of Natural History](https://www.expedia.ca/Carnegie-Museum-Of-Natural-History-Oakland.d6078701.Vacation-Attraction) - [Cathedral of Learning](https://www.expedia.ca/Cathedral-Of-Learning-Oakland.d6269525.Vacation-Attraction) - [Manor Theatre](https://www.expedia.ca/Manor-Theatre-Squirrel-Hill-South.d553248621532660405.Vacation-Attraction) - [Phipps Conservatory](https://www.expedia.ca/Phipps-Conservatory-Central-Oakland.d6078683.Vacation-Attraction) - [Visit East Liberty](https://www.expedia.ca/Pittsburgh-East-Liberty.dx6343585) - [Visit Friendship](https://www.expedia.ca/Pittsburgh-Friendship.dx553248632556594132) - [Visit Greenfield](https://www.expedia.ca/Pittsburgh-Greenfield.dx553248635976476814) - [Visit Middle Hill](https://www.expedia.ca/Pittsburgh-Middle-Hill.dx553248635976477076) - [Visit Stanton Heights](https://www.expedia.ca/Pittsburgh-Stanton-Heights.dx804079386502275072) - [Visit Terrace Village](https://www.expedia.ca/Pittsburgh-Terrace-Village.dx804080730279682048) - [Visit Upper Hill](https://www.expedia.ca/Pittsburgh-Upper-Hill.dx804080657100279808) - [Schenley Park](https://www.expedia.ca/Schenley-Park-Squirrel-Hill-South.d6078717.Vacation-Attraction) - [Upmc Shadyside](https://www.expedia.ca/UPMC-Shadyside-Shadyside.d6269693.Vacation-Attraction) - [University of Pittsburgh](https://www.expedia.ca/University-Of-Pittsburgh-Oakland.d6090505.Vacation-Attraction) - [Car rentals near Carnegie Mellon University](https://www.expedia.ca/Car-Rentals-In-Carnegie-Mellon-University.d6090503.Car-Rental-Guide) - [Things to do in Pittsburgh](https://www.expedia.ca/Things-To-Do-In-Pittsburgh.d601717.Travel-Guide-Activities) - [Book Hotels in Shadyside on Expedia.com](https://www.expedia.com/Shadyside-Pittsburgh-Hotels-Luxury-Hotel.0-n6156339-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)