If you’re longing for a getaway but can’t stray too far from the ‘Burgh, the cozy little cliché known as a staycation is an excellent choice. But in this case, we’re not just talking about any stay – we’re talking enveloping lodging that feels like stepping back in time. That’s right, adventure doesn’t always require a plane ticket, and sometimes your mode of transportation can be an imaginary time machine.
Pittsburgh’s glorious past is reflected in its stunning bridges, iconic museums and opulent heritage hotels. The trademark Pittsburgh architecture and classic furnishings of said residences let you experience Pittsburgh’s opulent past while enjoying modern conveniences. It is a unique way to immerse yourself in the city’s rich history and culture, making your visit an unforgettable journey through time. No DeLorean required – just your curiosity.
We’ve put together a list that will make you appreciate the magic of exploring your own backyard during the colder months. Pack your bags (or not, since you’re not really going anywhere) and get ready to fall in love with the city all over again. Gear up for a unique adventure that bridges time and place.
Omni William Penn Hotel
Where Gatsby-like extravagance awaits classic novel enthusiasts
530 William Penn Pl. Downtown. omnhotels.com
There have been many cool openings in the Pittsburgh hotel scene over the past decade, but the Omni William Penn Hotel in downtown Pittsburgh still offers something different: pure old-school opulence. The hotel, which opened in 1916, has seen its fair share of famous guests, including one young bandleader named Lawrence Welk – who would later gain fame for his eponymous TV show. In fact, Welk performed in the hotel’s various ballrooms, and the hotel’s engineers even helped produce Welk’s iconic bubble machine. Omni William Penn has also hosted every sitting president since Theodore Roosevelt. Several US presidents have even campaigned inside the building at one point or another, including Harry S. Truman, Lyndon B. Johnson and Ronald Reagan.
So it’s telling that the place is shrouded in history, right down to the details – think crystal chandeliers in the lobby, shiny marble floors and intricate woodwork in the corridors. The 597 well-appointed rooms and suites offer cherry wood furnishings and stunning views of downtown through large windows.
When the cold sets in, you can cozy up in the lobby with a steaming hot cocoa. For something stronger (a hot toddy?), served with a side of nostalgia, step into their Speakeasy, a throwback to the Prohibition era. Nearby you can enjoy top restaurants such as Eddie V’s, The Capital Grille and Proper Brick Oven.
The inn at Negley
Where you will discover a Victorian retreat straight out of a Jane Austen novel
703 S. Negley Ave., Shadyside. innonnegley.com
The biggest draw for the Inn on Negley is its prime and very picturesque Shadyside location. But once there, this charming Victorian-style B&B is like a step back in time, where antique fireplaces, period decor and a serene garden make you forget you’re in the city. Built in 1884, this 8-room luxury inn oozes history and charm. With 25 years of expertise, innkeeper Elizabeth Sullivan ensures that your stay is top notch. Step outside and there is effortless access to the area’s finest restaurants and shopping. Explore Shadyside’s lively streets, indulge in culinary delights, and shop stylish boutiques – all within walking distance. After a brisk walk through the neighborhood’s colorful foliage, there’s nothing like retreating to your room and basking in the warmth of a roaring fire, all while tucking into some wine and cheese.
Photo by Roy Engelbrecht, courtesy of The Parador Inn
Parador Inn dining room
The Parador inn
Where your inner Jack Sparrow comes to life
939 Western Ave., North Side. theparadorinn.com
Escape to The Parador Inn on Pittsburgh’s North Shore—a restored 19th-century mansion that’s now a Caribbean-inspired bed and breakfast. Owned by seasoned hospitality pro Ed Menzer, this tropical oasis in the heart of the city is a must-visit. Stroll through lush gardens, discover charming historic nooks and keep an eye out for the surprising tropical creatures in quirky murals. Whether relaxing in the Lake Worth Sun Room (which boasts a waterfall brought up all the way from Lake Worth, Florida!), plotting world domination in the library or sipping a glass of wine by the fireplace in the formal living room, the is pure grandeur with a Caribbean twist.
Photo by Roy Engelbrecht, courtesy of The Parador Inn
Parador Inn dining room
Priory Hotel
Where history buffs can experience a Downton Abbey-inspired holiday
614 Pressley St., North Side. thepriory.com
Older Pittsburghers may have a soft spot for The Priory Hotel, a 42-room historic boutique hotel located on the thriving North Shore, just minutes from Downtown. Today, however, it is also a big hit with the Instagram generation. Once a Benedictine monastery dating back to 1888, it has been lovingly restored to its 19th-century elegance by the Graf family, who gave it a modern makeover in 2011 and a fresh facelift in 2021-2022.
The lobby’s soaring ceiling, stained glass windows and gilded columns are reminiscent of a bygone era. There’s also plenty of historical charm in the bedrooms, with ornate headboards and vintage photographs that offer a glimpse of Pittsburgh’s past. With cozy rooms filled with antiques and period reproductions, it’s an escape with character. In the evening, you can cozy up in your room with a book or soak in the bath with the claw. The Grand Hall, a former church, provides a unique touch for special occasions.
Speaking of special, Monk’s bar, their in-house bar is known for making some particularly wicked craft cocktails. But what makes the Priory really stand out is the personal service that treats guests with individual care. While most hotels will boast of impeccable service, this hotel actually walks the talk, whether it’s champagne deliveries for special occasions, surprise upgrades or even custom pillow types.
The carpenter hotel
Where you can enjoy a Sherlock Holmes-worthy stay, modern yet vintage chic
453 Boulevard of the Allies, Downtown. joineryhotel.com
For a taste of modern Pittsburgh, The Joinery Hotel is a must. The hotel seamlessly blends industrial aesthetics with modern luxury. Steel beams and exposed brick create an atmosphere that reflects the city’s industrial heritage. As you explore, admire the local artwork that adorns the walls, a nod to Pittsburgh’s thriving art scene. With a picturesque red brick facade, an opulent lending library and a dreamy rooftop, it’s very much the epitome of Pittsburgh.
The location is second to none – 2 blocks from the Monongahela River, a 5 minute walk from a metro station and 3 miles from the Carnegie Museum of Art. Located in the Golden Triangle, it’s a good base for exploring your own city with the eyes of a tourist. Whether you’re browsing Point State Park, catching a game at PNC Park, or enjoying the Ted Lasso omelet at the Speckled Egg, you can easily hit all of these spots.
Speaking of eggs, Christian James, the hotel restaurant offers a pretty wicked brunch – breakfast burrito with scrambled eggs, the sunny side up breakfast burger and delicious smoothies. The dinner menu and wine list are also quite impressive. Spend your stay exploring the local art scene, dining at nearby eateries, and embracing the city’s vibrant culture.