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...

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...

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...

The Candlelite Inn is a beautifully preserved 190-year-old Victorian inn situated on one and a half acres in the center of Shelter Island. Recently redecorated with care and an eye for period detail, The Candlelite Inn offers five guest rooms with private baths, central air conditioning, and a continental breakfast served each morning. The stunning wraparound porch is perfect for Read more...

Dering Harbor Inn is a classic Shelter Island retreat offering comfortable, well-appointed rooms and suites in a tranquil setting overlooking the harbor. Known for its beautiful grounds, welcoming atmosphere, and stunning water views, Dering Harbor Inn has been a favorite among East End travelers for decades. The property features an outdoor pool, spacious rooms, and a location that puts guests Read more...

Chic boutique hotel with a French Riviera feel right on the water. Hip, stylish, and uniquely Shelter Island. Read more...

Iconic waterfront resort on Crescent Beach with stunning views and a rich history. The quintessential Shelter Island summer destination. Read more...

Shelter Island’s beloved Victorian hotel founded in 1872. A true island landmark in the Heights with charming rooms and a celebrated restaurant. Read more...