A casual retreat welcomes visitors to its sunny isle.
Shelter Island is a one of the most laid-back destinations on the northeastern seaboard, and The Chequit its quintessential inn. Nestled between Long Island’s North and South Forks, the island has a refreshing lack of pretension, providing an ideal spot for a couple of enterprising hoteliers to set up shop. When an 1872 Victorian came on the market in 2014, the co-owners of Salt Hotels, David Bowd and Kevin O’Shea, jumped at the chance to reimagine it as an elevated bed-and-breakfast. Considerable work went into reinventing the aging edifice as a 37-key hotel, but the pair took care to preserve the building’s original character in the process. Décor is sparse, composed of wrought-iron beds, Turkish throws, and brass bedside lighting. The aesthetic is simultaneously considered and laissez-faire, contemporary and antique. A similar charm defines Red Maple, the on-site restaurant. The venue’s interior, all patterned wallpaper and whitewashed antiques, opens onto an expansive wooden terrace. There, the platform encircles the venue’s centerpiece: a namesake maple tree, draped in fairy lights—a picturesque spot to spend a hot midsummer night.