The Pridwin Hotel & Cottages

Perched above the gentle curve of Crescent Beach, The Pridwin Hotel & Cottages feels like a throwback to the golden age of East Coast summering—where city escapists and generations of families collide against a backdrop of salt air, tennis courts, and Gatsby-era nostalgia. The sunlight streams through country-chic rooms and private cottages, each space meticulously revived but not stripped of its quirks. Days begin with yoga on the lawn and farm-fresh omelets, then drift into kayaking or lounging poolside with lemon ice in hand. By dusk, fire pits flicker along the water’s edge and live bands play as guests feast on barbecue overlooking the bay. Here, tradition is honored but never stuffy: staff hail from across the globe, mixing warmth with easy professionalism. Locals drop by for Wednesday night BBQs while visitors savor the slow rhythm unique to Shelter Island. This isn’t just a hotel—it’s a living piece of Long Island’s summer lore, bridging old-school Americana with modern comfort.