The grand horseshoe of a driveway at the 19th-century brick and limestone mansion, which is decked with a marble fountain whose slabs were meticulously imported piece-by-piece from Italy, is enough to make you forget you’re only three hours from New York City. In reality, you’re on 22 manicured acres of lush parkland—landscaped by the great Frederick Law Olmsted, of Central Park fame—that are a couple of miles from the cultural hotbed of Lenox, Massachusetts, an archetypal Rockwellian town that’s the site of the famed music venue, Tanglewood, and summer home to the Boston Symphony Orchestra. Originally built as an over-the-top wedding gift for the daughter of a wealthy New York City financier and real estate tycoon circa 1893, this Italian-revival resort was completely overhauled in 2002 when Manhattan-based architects, Calvin Tsao and Zack McKown were tapped to usher it into the 21st century. That thoughtful four-year renovation resulted in the reconfiguration of all 19 guest rooms (no one exactly resembles the other) where a restrained and postmodern aesthetic, consisting of clean lines and soothing honey-hued fabrics, are complemented by antique embellishments, like vaulted plaster ceilings, Venetian mirrors and oversize claw-foot tubs, salvaged from an old English spa. The most striking example of this newfound rural minimalism, though, is the refreshed courtyard, where the addition of glass panels between Palladian columns converted a popular summer haunt into a stunning all-weather dining space.
It’s easy to imagine a digital-age Jay and Daisy languidly sipping Gin Rickeys at the Great Hall, or hosting a soiree by the outdoor heated pool.
With its Tiffany stained glass windows, sweeping staircase, and 24-karat gold encrusted china, The Wheatleigh is rife with reverential nods to a bygone era. But that doesn’t mean it’s trapped in the past. Continental hospitality hallmarks, such as fastidious and personalized service (upon check in, a staffer visits your suite and offers you a vast array of toiletry sets to choose from; at breakfast, hot chocolate is poured from a silver pot), courtesy of a predominantly Europe-trained staff, and museum-worthy art, including sculptures by Ruth Duckworth and canvases by landscape artist Bart Elbach, are infused with a decidedly unfussy elegance.
It’s easy to imagine a digital-age Jay and Daisy languidly sipping Gin Rickeys at the Great Hall, the hotel’s regal foyer and parlor hybrid, engaged in an impassioned tête-à-tête inside the roomy wine cellar, or hosting a soiree by the outdoor heated pool. From July through August, the resort treats guests to a weekly midsummer night’s barbecue on its upper terrace, complete with live jazz and grilled lobster.
The summer months also often showcase thematic tributes to past celebrity guests, like Leonard Bernstein—rumor has it his piano was squeezed into the resort’s living room. The legendary music man was a regular guest of The Wheatleigh’s sought-after two-floor suite, a former aviary with a sculptural glass staircase and a dreamy bedroom that’s practically nestled in the surrounding, century-old trees.