July 3, 2025

The Maidstone Hotel—Where Hamptons History Meets Quiet Luxury

Hotel Snapshot

Perched on a pristine lawn along East Hampton’s Main Street, The Maidstone is a storied hideaway that has charmed visitors for over 150 years. A historic inn reimagined by LDV Hospitality, the boutique property has evolved from a traditional Hamptons B&B into a design-forward stay that nods to both its Scandinavian roots and its new Euro-chic flair.

With just 16 guest rooms and an inviting restaurant and bar, The Maidstone now draws a stylish crowd, thanks to curated fashion pop-ups, intimate dinners, and creative programming. It’s a perfect marriage of old-school New York affluence and modern-day luxury, where the past lingers, but the present leads.

Design & Character

White-washed shingles, blooming hydrangeas, and classic Cape Cod charm set the scene at The Maidstone. The historic bones are intact, but LDV Hospitality has polished every corner to match the brand’s contemporary aesthetic. Inside, the “lobby” evokes a well-styled living room rather than a grand foyer—cozy corners with fireplaces, antique upholstery, and shelves stacked with art books and newspapers encourage lingering.

Guest hallways feature woven carpet runners and bold abstract paintings, evoking the aura of an art collector’s seaside home. Through September, rotating exhibitions celebrate La Dolce Vita, adding another thoughtful touch to the ever-evolving interiors. From the outside, it may seem like your classic Hamptons hideaway—but inside, The Maidstone blends old-world character with playful, stylish elegance. Whether you're curled up with a book or sipping a Negroni by the fire, every inch is crafted to make you right at home—and just a little glamorous.

The Rooms

The Maidstone’s 19 rooms—comprising 16 guest quarters in the main house and three standalone cottages—embrace a minimalist-meets-vintage style sensibility, offering a sense of cozy refinement. It feels more like staying at your chicest friend’s Hamptons guesthouse than a traditional hotel. I stayed in Room 12, tucked on the top floor’s right side, where sunlight spilled through traditional windows onto natural wood floors, a king-sized white linen bed, and a tucked-away daybed nook.

Thoughtful touches abound—vintage alarm clocks, a retro baby-blue Frigidaire, and plush seating complete the understated aesthetic. In the bathroom, a freestanding tub offers a perfect view of the front lawn, ideal for post-beach bubble soaks. A green-and-brown tiled shower with stellar water pressure gives it a spa-like appeal.

Each guest receives a handwritten note, and extras like a Steamery iron, terry robes, and embroidered slippers make you feel perfectly cared for. You’ll also find a white linen pajama set and a branded beach tote available for purchase—proof that thoughtful details here are anything but an afterthought.

Food & Drink

The Maidstone’s restaurant feels more like an elegant dining room than a traditional eatery. Tucked behind the front bar, it features intimate tables, a cozy back booth by the fireplace, and dimly lit sconces that cast a warm glow. Framed photos of vintage Italian cars and coastal scenes set the tone—New York cool meets Mediterranean romance.

Start with a cocktail (or two). The Maidstone Spritz blends Tanqueray Ten, St. Germain, Prosecco, and pink grapefruit for an elevated twist on a classic. The Lychee Sgroppino, with Ketel One and lychee purée, is a sweet ode to summer. Zero-proof options, such as the Ginger Highball (ginger ale, syrup, and lime), are equally refreshing.

My waiter, Iggy, recommended the scallop crudo—delicate slices layered with white asparagus vinaigrette and caviar. It was divine. The charred zucchini salad was another standout, with Castelrosso cheese and a citrusy jus over grilled squash.

For the main: the iconic “Scarpetta” Spaghetti, a 20-year menu staple. Made with San Marzano tomatoes and fresh basil, the slow-cooked sauce is reminiscent of a beloved Nonna’s recipe—simple, rich, and deeply satisfying.

I ended the meal with a scoop of pistachio ice cream—creamy, nutty, and garnished with toasted pistachios. Sweet, cold, and just right.

Amenities

Start your morning with a complimentary breakfast spread in the living room—think bagels and lox, charcuterie, pastries, yogurt, and fresh coffee. In the rooms, ladies will be pleased to find GRD blow dryers and flat irons (yes, finally a hotel with good hair tools!), Angeli di Firenze soaps, and grooming kits for anything you forgot.

Location & Neighborhood The Maidstone Hotel — Credit: Letizia Cigliutti

Location & Neighborhood Recs

To feel like New York’s elite, you stay in East Hampton. The Maidstone is centrally located on Main Street, just a short walk from high-end staples like Veronica Beard, Brunello Cucinelli, Loro Piana, and the iconic two-story Gucci boutique. Locals frequent Citarella for gourmet groceries, while Cult Gaia and Manolo Blahnik offer fashionable temptation nearby.

The beach is just five minutes away by bike—cruisers are available for guests—and if you’re staying during the summer, keep an eye out for designer pop-ups in The Maidstone’s backyard, like this season’s Sézane shopping experience.