The Roundtree

Low-key luxury in the Hamptons is increasingly rare, which is what makes The Roundtree, a two-and-a-half-hour-drive from New York City, such an extraordinary find. Located in the small hamlet of Amagansett (in between East Hampton and Montauk), the 13 room property is set on two beautifully landscaped acres and features a collection of renovated cottages and houses. The setting exudes classic Hamptons charm: think shingle-style exteriors, hydrangea-lined walkways and design references to Amagansett’s farm-steading legacy (this property itself was once a working farm).

Everything is clustered around the sprawling, manicured Great Lawn, tricked out with white umbrellas and cushy sun loungers, lawn games (cornhole, anyone?) and a cozy fire pit where guests gather for night caps and stargazing. Perhaps most importantly, it allows guests to feel like Amagansett residents (if only for a night, a week, however long their stay).

Why Amagansett? While East Hampton and Southampton are bustling towns, Amagansett’s small main street is quaint and only has a handful of shops and restaurants. (For reference, the population of next door East Hampton is nearly 29,000 while Amagansett under 1,000.) One can meander down the street to local favorite Amber Waves, part-farm -market and -café, have a meal at Il Buco al Mare, and check out the line-up at old-school music venue Talkhouse. The Roundtree’s resident Experiences Director makes the most of the area by creating special excursions for guests, like private beach bonfires. The fall is also an insider favorite – traffic and crowds are gone, the farmstands are in full force will fall’s bounty (pumpkins, roasted corn, greens, apples and cider donuts…), beaches are empty for walks or sunny day picnics, and restaurants have plenty of reservations. The Hamptons Film Festival is a buzzy fall tradition, as well as Montauk’s Fall Fest with its clam chowder contest and local food trucks.