By Lindsey Olander
Updated: January 24, 2017
Courtesy of Salt Hotels

Hoteliers Kevin O’Shea and David Bowd, the same guys behind Provincetown’s buzzy and beautiful Salt House Inn, have done it again, opening a 37-room refuge on New York’s windswept Shelter Island. The Chequit, which opens its doors May 8, was designed for the dreamy summer jaunts to the East End. Here’s why it’s become an obsession:

The Design: Whitewashed rooms, bathed in natural light, are luxuriously spare, pulling in a combination of colorful Turkish throw rugs, brass lighting fixtures, and a soothing nautical palette of pale blues, pinks, and whites. Wide-brimmed straw hats hang on reclaimed ladders. Succulents and live flowers dot guest room tables.

The History: First built as a religious retreat in 1872, the property transformed into a high-society getaway in the 1940s, visited by the likes of Frank Sinatra and Marilyn Monroe.

The Details: True original antiques (bureaus, side tables) were saved from the old property for use in the satellite lodge, dubbed the Summer House. Speaking of which…

The Summer House: The six-room neighboring cottage is rentable by room or by group—for the day, week, even the entire summer. The look: a Moonrise Kingdom-type of fashionably lived-in goodness. What’s more, rooms go for $195 a night—a price basically unheard of in these parts.

The Shop: Bridgehampton-based sporty retailer Wampum has opened an outlet here, where guests can pick up essential surf-chic accessories—hats, wallets, t-shirts—emblazoned with a signature print created for the hotel. Psst: Wampum also designed the staff uniforms, natch.

The Location: Set among a clutch of Victorian cottages on a quiet hilltop on idyllic Shelter Island, nestled between Long Island’s North and South Forks, the Chequit offers a true escape from the congested sands of the Hamptons.

The Food: The perfectly shareable plates served at restaurant Red Maple are all about to-die-for flatbreads (oven-dried tomato, wild mushroom, smoky bacon and clam) and locally sourced produce—think Montauk fluke crudo, South Fork asparagus, and Fisher’s Island oysters. Too antsy to hit the beach? West Village mainstay Jack’s Stir Brew and hot fresh pastries from Baked are continually replenished at the grab-and-go coffee bar.

The Perks: No “we can’t seat you until your whole party is present” restaurant malarkey. Also, guests can get breakfast in bed—with no delivery fee. Best of all? No set check-in time.

Lindsey Olander is an Assistant Editor at Travel + Leisure. Follow her on Twitter and Instagram at @lindseytravels.