The Roundtree, Amagansett Review

There’s an undeniable magic to East Hampton, where the light is cinematic, and the dunes are pristine. In Amagansett, a bohemian town that wears its affluence well, the vibe is understated and just slightly aloof—it’s a place where famous faces can retreat in anonymity, even when strolling the glorious farmer’s market, or perusing the latest bestsellers at the local bookstore. It might all seem like a movie set, an impression furthered by a peek at The Roundtree. This intimate, 14 room, boutique hotel, just off of Main Street, looks like the setting for a Nancy Meyers movie.

Spread across two bucolic acres, and within 17th-century structures, The Roundtree blends heritage with modernity, and rural calm with coastal sophistication. Accommodations range from guest rooms and suites to standalone cottages—each distinct, yet united by the Meyers-like aesthetic of creamy neutrals. Interiors are muted, warm, and organic: bleached wood floors, soft textiles in calming tones, understated furnishings, and curated details that feel personal rather than performative. Each accommodation is equipped with cozy Frette linens, Malin + Goetz bath amenities, plush robes, rainfall showers, and thoughtfully stocked minibars. Cottages feature separate living areas and private outdoor space, ideal for families or longer stays. Art is used sparingly—vintage photography, abstract line drawings, a scattering of coffee table books that reflect the region’s cultural undercurrent. The overall effect is serene, with a touch of intentional simplicity.

The Roundtree’s premier accommodation is the Beach House, located just five minutes away in the prestigious Amagansett Dunes neighbourhood. Built in the 1960s by renowned East Hampton architect Alfred Scheffer this retreat was originally owned by the famous Tony Award-winning playwright Neil Simon. Rumor has it that he wrote Barefoot in the Park here, as well as Lost in Yonkers, and Brighton Beach Memoirs, among other classics. Once you experience the golden hush of twilight over the ocean from this enchanting locale, you’ll understand exactly why inspiration struck here. The expansive 2,700 square foot retreat features four bedrooms, five bathrooms, a wood-burning fireplace, outdoor shower, and an inviting patio for grilling, dining, and lounging. The local beach, which stretches for miles on end, is a short walk away and accessible by private pathways. (During the summer season, two week minimum stays are required for the Beach House.)

At The Roundtree, there is no formal front desk or bustling lobby. Instead you are greeted personally, often with refreshment in hand, and led through the leafy property to your accommodations. The welcome is sincere and relaxed, with none of the transactional formality of a larger hotel. A member of the staff offers a quiet walkthrough of the guest room, shares a few recommendations, and then disappears, leaving a sense of complete privacy. Luxuriate in your quarters, or head to one of the discreet outdoor seating areas, or a tree-hung hammock to acclimate upon arrival.

Each evening you’ll receive a text message with a link to a menu from which to select continental breakfast items to be delivered in a picnic basket to your accommodations. Enjoy in room or al fresco on the property’s grounds, weather permitting. You’ll also receive daily turndown service that includes weather cards for the following day. In the afternoon, homemade cookies appear in communal spaces. Bicycles, beach chairs, towels, and umbrellas are available for use, and the hotel will gladly arrange for a full beach setup on request. Pets are also welcome and accommodated with beds, bowls, and treats. Additionally, your stay includes ice cream socials courtesy of a local creamery, s’mores kits to be enjoyed at the lawn firepits, and a bevy of evening snacks to satisfy late-night cravings.

The Roundtree’s location is one of its greatest assets. It sits just off Amagansett’s village centre, within walking distance of cafes, shops, and that amazing farmers market. A short bike ride brings you to the Atlantic—either Indian Wells Beach or Atlantic Avenue Beach. Nearby, the natural landscape unfolds across walking trails, preserves, and meadows. Wolffer Estate Vineyard (and its fantastic Chardonnays) is an easy drive, as are local galleries. Montauk, with its windswept beaches and surf culture, is less than 20 minutes away. But you’ll not be faulted for simply settling in at The Roundtree, where the pace is unhurried and the atmosphere is insulated from the busy rhythms of summer in the Hamptons.

The local culinary scene hums of coastal flavour and local character and everything is within walking distance to the hotel. Nearby il Buco al Mare is a great place from which to order room service. Rowdy Hall features comfort food with an edge, and legendary bar Stephen Talkhouse comes to life in the evening with live music and local colour.

With its unique blend of style, comfort, and local charm, The Roundtree is the perfect base for exploring the Hamptons or simply unwinding in a beautiful setting. Thoughtful amenities, a welcoming atmosphere, and a prime location ensure that a Roundtree stay is more than memorable; it’s inspirational.

Image Credits: The Roundtree