Want to know where to eat? Where to shop? Where to stay? What to do? Are you curious about special events on Shelter Island? Our Business Directory has all the information you need.

The Best Shelter Island Hotels, Inns, and Bed & Breakfasts

Shelter Island has a wide variety of accommodations, so it’s easy to match any visitor’s preferences. Whether you desire the lively atmosphere of a waterfront resort, the quiet of a secluded bed and breakfast, or the charm of an historic inn located in the heart of the island, Shelter Island's accommodations are as diverse as the experiences they promise. Explore this guide to some of our best Shelter Island hotels and find the perfect match for your budget, style, and island adventure dream.

Avalon Manor Bed & Breakfast at Chase Creek
(directions)

Avalon Manor, at Chase Creek on Shelter Island, is a picturesque bed and breakfast that epitomizes the quaint charm and serenity of island life.

This enchanting establishment offers guests a blend of historical allure and contemporary comforts, with each room meticulously designed to provide a peaceful and intimate atmosphere. The manor is set against a backdrop of stunningly manicured gardens, perfect for leisurely strolls or quiet contemplation. Guests praise the warm hospitality and personalized service, ensuring a memorable stay. Avalon Manor is an ideal choice for those seeking a tranquil escape, with ample opportunities to explore the natural beauty and cultural heritage of Shelter Island. For booking and further information, visit Avalon Manor’s website.

Belle Crest Inn, Shelter Island Heights
directions

Just a short walk to shops and restaurants on the north side of the island, The Belle Crest Inn stands as a testament to timeless elegance and comfort, inviting guests into a world where traditional charm meets contemporary convenience.

This historic inn offers a range of accommodations from cozy rooms to spacious suites, each thoughtfully designed to ensure a relaxing stay. Guests are encouraged to unwind in the common areas, enjoy the outdoor spaces, and explore the island's attractions. The Belle Crest Inn emphasizes personalized service and a warm, welcoming atmosphere, making it a perfect choice for travelers seeking a tranquil retreat. Visit their website for more details and to book your stay: Belle Crest Inn.

Dering Harbor Inn
directions

The Dering Harbor Inn, located on Shelter Island's scenic waterfront, offers an idyllic setting for guests seeking relaxation and outdoor activities.

With its location offering easy access to both the island's nature trails and vibrant small-town life, this inn provides the perfect balance of seclusion and connectivity. Guests can enjoy modern accommodations with panoramic views, an outdoor pool, and tennis courts. This inn serves as a peaceful retreat for those looking to explore the island's charm or simply unwind by the water. For more details, visit their website at Dering Harbor Inn.

House on Chase Creek
(Town Landing)
directions

House On Chase Creek blends historical charm with modern comfort, emphasizing the warmth of original pinewood floors and carefully selected antiques.

This balance ensures guests enjoy both timeless aesthetics and contemporary conveniences. Its location offers easy access to Shelter Island's highlights, including beaches, dining, and outdoor activities, making it an ideal base for exploring. The inn promises a tranquil retreat throughout the year, highlighting the beauty of each season from the vibrant spring blooms to the serene snowscapes of winter. For more information on what makes the House On Chase Creek a special place to stay, visit their website at House on Chase Creek.

The Ram’s Head Inn
(Town Landing)
directions

Sitting atop a hillside, the Rams Head Inn is known as a chic yet historic and inviting seaside getaway.

The Rams Head Inn offers a serene and luxurious getaway on Shelter Island, blending elegance with the natural beauty of its surroundings. This historic inn is renowned for its gracious hospitality, offering guests an array of amenities including fine dining, tennis courts, and a private beach. With its stunning waterfront views and beautifully appointed rooms, the Rams Head Inn is a perfect retreat for those seeking relaxation and tranquility in a picturesque setting. For more details on accommodations and services, visit their website at The Rams Head Inn.

Seven On Shelter
(Town Landing)
directions

Seven on Shelter is a stylish traveler's dream, redefining the classic bed and breakfast experience on Shelter Island.

This award-winning, newly restored inn is a stone's throw from Crescent Beach. It pairs the charm of a 1902 whitewashed farmhouse with modern luxuries, including a heated pool and cabana, bikes, croquet, and a serene space for yoga and meditation. Its contemporary design and array of amenities promise a tranquil and lavish retreat. Perfect for those seeking a discreet yet indulgent escape near the Hamptons. For more about this reimagined stay, visit Seven on Shelter.

The Chequit
directions

The Chequit Hotel offers an intimate and historic retreat on Shelter Island, blending timeless charm with modern comforts.

This beautifully restored inn is celebrated for its cozy accommodations, welcoming atmosphere, and attentive service. Guests can enjoy a range of amenities, from delightful breakfasts to serene outdoor spaces. It's an ideal spot for those seeking a peaceful getaway with a touch of nostalgia. The Chequit promises a memorable stay, making it a standout choice among Shelter Island's lodging options. For details on staying at this unique property, visit The Chequit Hotel.

The Pridwin Hotel & Cottages
directions

The Pridwin Hotel offers a classic vacation experience with a touch of vintage charm.

This waterfront property boasts stunning views of Shelter Island Sound, providing guests with a serene setting for relaxation. Amenities include a private beach, outdoor pool, and dining options that showcase local seafood. Ideal for families and couples, The Pridwin promises a mix of relaxation, recreation, and classic summer pleasures. After recently undergoing a comprehensive renovation, The Pridwin Hotel reemerged as a blend of its timeless heritage with modern luxury. This revitalization enhanced its classic appeal while introducing contemporary amenities, ensuring a seamless experience of tradition and comfort. For details on its transformation and offerings, please visit The Pridwin Hotel.

Two South Ferry B&B
directions

Two South Ferry B&B offers a cozy, homely atmosphere for visitors seeking a tranquil stay.

Their four guest rooms are in a separate wing and each has its own private deck. The rooms open up into a common great room where an extended continental breakfast is provided daily. Located conveniently in the middle of the island, it allows easy access to Shelter Island's attractions. For example, the Shelter Island Historical Society is just a 3 minute walk down the road. The Nature Conservancy’s Mashomack Preserve is just a 15 minute bike ride away, where you can explore nature trails criss-crossing over the two thousand plus acre preserve. For more details on amenities, accommodations, and to book your stay, visit their website at Two South Ferry B&B.

The Candlelite Inn
directions

The Candlelite Inn offers a blend of historic elegance and modern comfort within its Victorian architecture.

Boasting five guest rooms with plush queen-sized beds and high-quality bedding, the inn ensures a cozy stay. Guests can unwind on the wraparound porch or in the unique Honeymoon Cottage, which features luxurious amenities for a romantic getaway. The inn is conveniently located in the center of the island near fine dining options, shopping, and outdoor activities. Emphasizing a serene experience, it’s a smoke-free property not accommodating pets, making it an ideal retreat for those seeking peace and privacy.

For more detailed information, visit their website: The Candlelite Inn.

An Island sheltered by Islands

This was the name given to Shelter Island by the Manhanset Indians, long before the first English settlers arrived in 1652. They must have had a peaceful and bountiful life, since the Island is protected from the worst of weather by the sheltering arms of the Long Island's North and South Forks. The surrounding waters yielded up a bounty of fish and water fowl, while the woods and fields were equally stocked with deer and other game. The Manhanset's are gone, but the Island remains, still peaceful, still protected, still bountiful. Nearly one-third of this 8000-acre Island is owned by the Nature Conservancy and kept in a forever-wild state.

Our three deep-water harbors each have a fully equipped marina and are welcome havens for those arriving by boat.

Access to the Island is by car ferry; from Greenport on the North Fork, a 10 minute run, or from Sag Harbor on the South Fork, only three minutes away.

Shelter Island is for those who seek respite from the noise and turmoil of city and suburban life. Careful zoning has preserved much of the Island's rural character. The 35 mph speed limit plus the gentle pace of life bring our visitors back to a time many have thought was gone forever. If the Manhanset Indians could return through a time machine, they would experience some culture shock, but they would recognize this island sheltered by islands as the one they knew so many years ago.

Discover our Beautiful Secluded Beaches

Learn about Historic Shelter Island • Information on How to Get Here and much more

Catch up on all our Events