Nantucket’s Best Boutique Hotel Gets a Nostalgic Reboot

Courtesy photo

If you’re a native New Englander, chances are, you stayed at the Beachside back in the day. I know I did, in my twenties—decades ago, on a girls’ trip one early-September weekend. Back then, it was what I remember referring to as “fine”—no frills, sun-faded bedspreads, and within walking distance to town and Jetties Beach. But the bottom line was that it was affordable, and my friends and I spent barely any time at the hotel—when we were there, we were either asleep or in a hungover haze.

The Beachside, however, has ushered in a new era, and it’s a place where you’ll definitely want to linger. First opened in 1966, the 100-room hotel was purchased in 2021 by Blue Flag Capital—the team behind Faraway Hotels. This season marked its first full summer in operation since a gut renovation and rebrand, and the results are nothing short of transformative, winning this year’s Best of Boston award for Nantucket’s Best Boutique Hotel.

In the gift nook by the reception desk, travelers encounter everything from healthy snacks and sunscreen to chic hats, sporty beachwear, and bags for beach gear.

“There was a lot of history in the name,” says Blue Flag cofounder Brad Guidi, who remembers hearing nostalgic stories from locals about their Beachside stays there decades ago. “When you ask people if they’ve stayed here, most say, ‘Of course—I stayed there thirty years ago!’” Alongside business partner Jason Brown, who has three children, Guidi sought to reimagine the hotel with families in mind. “We’ve traveled with our kids,” he says of his wife and their son and daughter. “We designed a place where we’d want to stay with them.”

That philosophy permeates every inch of the 3.5-acre property, from its open-air courtyard and new mahogany pool deck to the cozy, seafoam-green indoor-outdoor bar. “We focused on creating outdoor spaces where discovery is limitless,” Guidi says. “This self-driven experience is all part of the story. I think we can all relate to the first taste of freedom that summer offered us as children—that was the feeling that we tried to evoke at the new Beachside. We wanted to offer a space where children and their parents alike would equally enjoy the property.” There are bikes at the ready for guests to pedal off on at a moment’s notice, and daily programming includes lawn games, movie nights, fire pits for s’mores sessions, and even a retro-inspired arcade.

The décor celebrates Nantucket’s artistic era of the 1960s and ’70s, when artists and craftspeople viewed it as a creative haven; colors, including terra cotta, recall this period.

New York–based Parts and Labor Design brought the vision to life through a playful, 1970s-inspired palette of terra cotta, moss green, and sun-washed creams (there’s not a blue-and-white motif in sight!). In the lobby, cantilevered woven chairs, low-slung sofas, and a white-tiled fireplace feel more like a design-forward living room than a check-in desk. Guest rooms nod to Nantucket’s Arts and Crafts history with earthy textures, retro checks, custom furniture, and local artwork—including mosaics and watercolors by Rhode Island–based artist Sean Spellman.

There’s a bit of a throwback motor-lodge vibe to the guest rooms, all of which have direct exterior access off the open-air corridors. Each room has some sort of exterior living space: balconies or patios furnished with plush chairs for lounging and small café tables, just right for enjoying the complimentary coffee and homemade doughnuts the hotel offers every morning in the lobby. “This place feels old-fashioned but in a cool way,” my 12-year-old daughter commented on our stay as she snacked on cotton candy served impromptu by the pool one afternoon. I couldn’t have said it better myself.

Guests can order drinks via the window behind the bar without having to go inside. Waitstaff also offers service to those lounging by the pool.