Upscale shelter island lodging in New York

Seven - A Boutique B&B Hotel on Shelter Island is a charming and stylish lodging located at 7 Stearns Point Road in Shelter Island Heights, New York. This boutique hotel offers a unique and personalized experience for guests looking for a cozy and intimate stay. The beautifully decorated rooms and common areas create a warm and inviting atmosphere, perfect for relaxation and comfort. With its convenient location on Shelter Island, guests can enjoy easy access to the island's beaches, shops, and restaurants. Whether you're looking for a romantic getaway or a peaceful retreat, Seven is the perfect destination for a memorable stay.

Shelter Island House is a charming and cozy bar and lodging establishment located at 11 Stearns Point Road in Shelter Island Heights, New York. Nestled in a picturesque setting, this institution offers a peaceful retreat for guests looking to escape the hustle and bustle of city life. With comfortable accommodations and a welcoming atmosphere, Shelter Island House is the perfect destination for a relaxing getaway. Enjoy a drink at the bar or unwind in one of the beautifully appointed rooms, all while taking in the stunning views of Shelter Island. Experience the beauty and tranquility of this hidden gem in the heart of New York.

The Chequit is a charming and cozy establishment located at 23 Grand Avenue in Shelter Island Heights, New York. This institution offers a variety of services including a bar, cafe, restaurant, and lodging accommodations. Guests can enjoy delicious food and drinks in a relaxed and welcoming atmosphere. Whether you're looking for a place to grab a quick bite, enjoy a leisurely meal, or spend the night, The Chequit has everything you need for a memorable experience.

The Ram's Head Inn is a charming waterfront institution located at 108 South Ram Island Drive in Shelter Island Heights, New York. This historic establishment offers a unique blend of food, lodging, and dining experiences, making it the perfect destination for a relaxing getaway or special event. Guests can enjoy stunning views of the surrounding landscape while indulging in delicious cuisine at the on-site restaurant. Whether you're looking for a romantic retreat, a family vacation, or a picturesque wedding venue, The Ram's Head Inn has something for everyone.

The Pridwin Hotel & Cottages is a luxurious lodging institution located at 81 Shore Road, Shelter Island, New York, United States. The campus offers a serene atmosphere perfect for relaxation and rejuvenation. Guests can enjoy a water-view pool overlooking Crescent Beach, complimentary yoga sessions, tennis clinics, and access to the new Pridwin Spa for day spa treatments and massages. The Fitness Center is equipped with cardio and strength-training equipment for guests to use throughout their stay. Outdoor activities such as kayaking and stand-up paddleboarding are also available. The institution hosts special events like plein air landscape drawing and painting workshops, as well as Murder Mystery weekends with immersive storytelling and problem-solving activities. Complimentary high-speed WiFi is available throughout the grounds, and guests can enjoy daily breakfast at the Terrace restaurant. Transportation to Shelter Island is made easy with partnerships with Hampton Jitney and North Ferry, providing a convenient car-free travel option from New York City.

Winthrop Manor Ltd is a charming lodging establishment situated at 13 Winthrop Road in the picturesque town of Shelter Island Heights, New York. This historic manor offers a cozy and inviting atmosphere for guests looking for a relaxing getaway. The beautifully appointed rooms and suites provide a comfortable retreat, while the convenient location allows easy access to the island's attractions and activities. Whether you're seeking a romantic escape or a family vacation, Winthrop Manor Ltd is the perfect choice for your stay in Shelter Island Heights.

The Chequit Restaurant is a charming and historic establishment located at 23 Grand Avenue in Shelter Island Heights, New York. This cozy and inviting spot offers a unique combination of a bar, restaurant, and lodging all under one roof. Guests can enjoy delicious meals made with locally sourced ingredients, sip on handcrafted cocktails at the bar, and retreat to comfortable accommodations for a restful night's sleep. The Chequit Restaurant is the perfect destination for a relaxing getaway or a memorable dining experience in the heart of Shelter Island.