5 historic Pittsburgh staycations that feel like a time-warp | Pittsburgh City Paper

5 historic Pittsburgh staycations that feel like a time-warp

click to enlarge 5 historic Pittsburgh staycations that feel like a time-warp
Photo by Roy Engelbrecht, courtesy of The Parador Inn
Parador Inn courtyard

If you're yearning for a getaway but can't stray too far from the 'Burgh, that quaint little cliche known as the staycation is an excellent choice. But in this case, we're not just talking about any staycation — we’re talking immersive lodgings that feel 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 mirrored in its stunning bridges, iconic museums, and lavish heritage-style hotels. The trademark Pittsburgh architecture and classic decor of said accommodations let you experience Pittsburgh's opulent past while enjoying modern amenities. It's 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 curated 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. Buckle up for a one-of-a-kind adventure that bridges (pun totally intended) time and place.

Omni William Penn Hotel
Where Gatsby-esque 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 last decade, but the Omni William Penn Hotel in downtown Pittsburgh still offers something different: sheer, old-school style opulence. The hotel, which opened in 1916, has seen its fair share of famous guests, including a young bandleader named Lawrence Welk — who would later gain fame for his eponymous television show. In fact, Welk performed in the hotel’s various ballrooms, and the hotel's engineers even helped produce Welk’s iconic bubble machine. The Omni William Penn has also received every seated president since Theodore Roosevelt. Several U.S. presidents have even campaigned inside the building at one point or another, including Harry S. Truman, Lyndon B. Johnson, and Ronald Reagan.

It's on brand, then, that the place is enveloped in history, right down to the details — think crystal chandeliers in the lobby, gleaming marble floors, and intricate woodwork in the hallways. The 597 well-appointed rooms and suites offer cherry wood furnishings and stunning downtown views through large windows.

When the chill sets in, 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, enjoy top restaurants like Eddie V's, The Capital Grille, and Proper Brick Oven.

The Inn on Negley
Where you'll 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 you’re 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 your stay is top-notch. Step out and there’s effortless access to the area's finest dining and shopping. Explore Shadyside's lively streets, indulge in culinary delights, and shop at stylish boutiques — all within walking distance. After a brisk walk through the neighborhood's colorful foliage, there's nothing quite like retreating to your room and basking in the warmth of a roaring fire, all while tucking into some wine and cheese.

click to enlarge 5 historic Pittsburgh staycations that feel like a time-warp
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 1800s mansion that is a Caribbean-inspired bed & breakfast today. Owned by the seasoned hospitality pro Ed Menzer, this tropical oasis in the heart of the city is a must-visit. Stroll through lush gardens, uncover charming historic nooks, and keep an eye out for the surprise tropical critters in quirky murals. Whether you're chilling in the Lake Worth Sun Room (that 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 Parlor, it's pure grandeur with a Caribbean twist.

click to enlarge 5 historic Pittsburgh staycations that feel like a time-warp
Photo by Roy Engelbrecht, courtesy of The Parador Inn
Parador Inn dining room

The Priory Hotel
Where history buffs can experience a Downton Abbey-inspired getaway
614 Pressley St., North Side. thepriory.com

Older Pittsburghers might have a soft spot for The Priory Hotel, a 42-room historic boutique hotel located on the thriving North Shore, just minutes from Downtown. However, today, 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 pillars are reminiscent of a bygone era. There’s plenty of historical charm in the bedrooms too, with ornate headboards and vintage photographs that offer glimpses into Pittsburgh's past. With cozy rooms filled with antiques and period reproductions, it is an escape with character. In the evenings, cozy up in your room with a book or soak in the clawfoot tub. The Grand Hall, a former church, lends an exceptional touch to special occasions.

Speaking of special, the Monk’s bar, their in-house bar is known to craft some particularly wicked craft cocktails. But what makes the Priory really stand out is the personalized service that treats guests with individual care. While most hotels will boast impeccable service, this hotel actually walks the talk, whether it be special occasion champagne deliveries, surprise upgrades, or even customized pillow types.

The Joinery 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 contemporary luxury. Steel beams and exposed brick create an ambiance that reflects the city's industrial heritage. As you explore, admire the local artwork adorning the walls, a nod to Pittsburgh's thriving art scene. With a quaint redbrick facade, a plush lending library, and a dreamy rooftop, it's very quintessentially Pittsburgh.

The location is unbeatable — 2 blocks from the Monongahela River, 5 minutes walk from a metro station, and 3 miles from the Carnegie Museum of Art. Located in the Golden Triangle, it is a great base for exploring your own city with the eyes of a tourist. Whether leaf-peeping at Point State Park, catching a game at PNC Park, or savoring the Ted Lasso Omelette at the Speckled Egg, you can hit up any of these spots easily.

Speaking of eggs, Christian James, the hotel’s in-house restaurant offers a pretty mean brunch — breakfast burrito with scrambled eggs, the breakfast burger with a sunny side up, and delicious smoothies. The dinner menu and wine list are pretty impressive too. Spend your staycation exploring the local art scene, dining at nearby eateries, and embracing the city's vibrant culture.