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Shelter Island House is a beautifully appointed boutique hotel in Shelter Island Heights, offering graciously sized rooms with spa bathrooms, chic décor, and local art in an intimate, welcoming setting. The hotel features a seasonal outdoor pool, complimentary Wi-Fi and bicycles, and the kind of personalized service that makes every guest feel like a valued regular. Shelter Island House also Read more...

Seven on Shelter Island is the island’s top-rated boutique inn, an award-winning resort-style bed and breakfast that has been named one of the best hotels in the Hamptons for ten consecutive years. Set within a private enclave near Crescent Beach, Seven features destination-level amenities — a heated pool, private cabanas, complimentary bicycles, open-air yoga and meditation, and beautifully designed rooms Read more...

The Ram’s Head Inn is one of Shelter Island’s most treasured retreats, a historic waterfront inn sitting atop a hillside overlooking Coecles Harbor on 4.5 beautifully landscaped acres. With 13 elegantly appointed rooms featuring Frette bedding, a private beach with moorings, kayaks and paddleboards, and a farm-to-sea restaurant that draws diners from across the East End, Ram’s Head offers an Read more...

Finley’s Fiction is a charming Shelter Island bookshop specializing in fiction, with a carefully chosen selection that reflects genuine literary taste and a love of storytelling. The shop is the kind of place that reminds you why independent bookstores matter — knowledgeable, personal, and full of discoveries that an algorithm would never suggest. Whether you’re looking for the latest literary Read more...

Artists of Shelter Island is a collective gallery celebrating the extraordinary creative community that calls this beautiful island home. Showcasing paintings, photography, sculpture, and mixed media works by local and island-affiliated artists, the gallery is a window into the visual world that Shelter Island inspires. The work on display reflects the island’s remarkable natural beauty — its light, its landscapes, Read more...