Be it a pre-wedding escape with your bridal troupe or a post-wedding mini-moon with your new spouse, landing at the doors of the Pridwin Hotel and Cottages in Shelter Island, New York, will be the beginning of a special occasion. The white clapboard great house and its 16 cottages provide the same tony, laid-back vibe found in the Hamptons, the island’s nearby cousin, but without the to-do.

Established in 1927, the resort is set on 8 acres with tall, shady trees and manicured lawns that look out on the bay from an elevated perch on Crescent Beach. Much of its original charm has been retained after a two-year renovation, which was completed in 2022. Pridwin is the largest hotel on the island, and each of its 33 rooms has a warm, nostalgic air and is nattily appointed with eclectic, nautical finds. Lodging options include king rooms, some equipped with queen sleeper sofas, or truly stretch out with one of the stylish cottages, offered as studios, one- and two-bedroom spaces (some with additional sleeping lofts), decks, gas fireplaces and kitchenettes.

Ask about a spin around the bay on the property’s charter, and take advantage of yoga, water sports, tennis and, of course, the pool and beach. Visit the spa for relaxation and beauty prep, from body treatments, massages—including for couples—to facials.

The Crescent Bar, with playful striped awnings and cane-backed chairs, offers drinks and bites. The Terrace, an expansive, indoor/outdoor restaurant—where the food is rivaled only by the views—has an all-day menu of locally sourced Long Island fare. 

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