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As you arrive on the island, an immediate sense of calm washes over you. The narrow, winding roads guide you toward the hotel.

The Pridwin is situated on a stunning property featuring its own dock and private beach, surrounded by picturesque views of the marina and passing boats. Stepping onto the property, you are welcomed by the American flag waving on the lawn, accompanied by a majestic oak tree that stands at the entrance. The ambiance at The Pridwin is casual yet sophisticated, with khakis, denim, and polos becoming the unofficial uniform for guests seeking leisurely relaxation.

Guests are invited to start their day with a quiet moment at the dock or sipping hot coffee on the porch. Mornings at The Pridwin are designed for relaxation and slow-paced enjoyment, whether you choose to lounge or partake in various activities offered on-site.

For those looking to fill their days with fun and exercise, The Pridwin provides an impressive range of recreational options. Challenge friends or family to a match on the tennis court, which is also suitable for pickleball, or enjoy a game of corn hole or volleyball. The hotel features a beautiful pool—though the waters may be brisk—and a game room stocked with table tennis and darts for indoor entertainment. A second indoor game room will host your card or board games to challenge your traveling companions. 

Dining at The Pridwin is an experience in itself. The on-site restaurant serves classic American dishes crafted from locally sourced ingredients, ensuring each meal is a delicious reflection of the region’s culinary offerings. Whether it’s a hearty breakfast or an elegant dinner, the menu is designed to satisfy and delight. With its careful blend of old-world charm and contemporary luxury, The Pridwin is more than just a hotel; it’s a gateway to a simpler time, embodying the spirit of authentic, timeless hospitality.

For those looking to escape the hustle and bustle, The Pridwin Hotel on Shelter Island is a hidden gem that promises a memorable experience steeped in relaxation, fun, and rich history. Whether you’re lounging by the pool, savoring delicious local cuisine, or exploring the stunning surroundings, every moment at The Pridwin invites you to slow down, breathe deeply, and immerse yourself in the beauty of a bygone era—reimagined for the modern traveler.