Where to Stay on Shelter Island

The Chequit guest room
The Chequit. Courtesy of Discover Long Island

Shelter Island, New York is an excellent destination for a summer vacation. One of the things that people love about Shelter Island is the quaint and cozy atmosphere. Everything is within a short driving or cycling distance and although it may be small, there are quite a few hotels from which you can choose.

Shelter Island is nestled between the Hamptons and North Fork in New York state. With about 2,000 permanent residents and lovely scenery, you will have a fantastic vacation here. Every accommodation has its own charm and beauty. You can go right with all the inns, but The Chequit or Rams Head Inn will win your heart!

You should consider Shelter Island as your next holiday destination for many reasons. The weather is nice, everyone is friendly, and there are many things to do. Don’t worry if your budget is smaller. There are affordable accommodations available for you and even a few free places too! There’s something for everyone on Shelter Island.

Whether you’re looking for a romantic weekend getaway or a family vacation, Shelter Island has something for everyone. There’s plenty to do on Shelter Island, whether boating, golfing, or walking on the beach. And with its rich history and beautiful scenery, it’s no wonder why this small island is such a popular destination. Before you go, though, be sure to make reservations. Not all hotels are available year-round. 

The Chequit

The Chequit Exterior Shelter Island
The Chequit. Courtesy of Discover Long Island

The Chequit is a classic summer retreat off the coast of Shelter Island.

The inn, which has been recently renovated, has welcomed guests since 1872 and is one of only two full-service hotels on Shelter Island. Guests can choose from one of five rooms, each with its own character and amenities.

The rooms are all decorated in a traditional style, with antiques and throw pillows adding to the old-world charm. There’s also an outdoor swimming pool that guests can use while lounging on the lawns or relaxing by the beach. The Chequit closes for the winter, reopens in the spring, and is family-friendly and pet-friendly. 

Rams Head Inn

shelter island rams head inn beautiful new york towns long island
Courtesy of Ram’s Head Inn

The Rams Head Inn is one of the most popular spots in town, and it’s easy to see why. This elegant Victorian style inn is near the center of Shelter Island and offers 17 guest rooms with private baths or shared baths and balconies overlooking the town’s Main Street. The rooms offer modern amenities like king-size beds, flat-screen TVs, and Wi-Fi access — with an added touch of old-fashioned charm courtesy of antique furniture and Tiffany lamps.

The restaurant at Rams Head Inn serves breakfast in bed or on the porch — or simply enjoy a cup of coffee while taking in views of Gardiner’s Bay. Rams Head Inn is family-friendly and open year-round. 

Look out for a wide range of events that Rams Head Inn hosts throughout the year including Murder Mystery Dinners and holiday parties.

The Pridwin

Pridwin Shelter Island exterior
Credit: Pridwin

The hotel’s location on Shelter Island makes it easy to explore and enjoy its many restaurants, shops, and beaches. The recently renovated hotel is family-friendly, though pets are not allowed. Amenities include a saltwater pool, a heated pool, a spa, a wellness center, a sauna, massages, and more. Pridwin of Cape Resorts has been serving guests since 1927 and is located on 10 acres on Crescent Beach. 

Sunset Beach Hotel

Sunset Beach Hotel is a seasonal hotel located on Shelter Island. Amenities include free Wi-Fi access throughout the property, air conditioning, and more. The Sunset Beach Hotel also offers catering services for weddings or other special events held at the property or off-site locations such as local vineyards or restaurants in town. Sunset Beach Hotel is a family-friendly location. 

Seven on Shelter

Seven on Shelter hotel is a luxurious and picturesque boutique hotel that offers guests a tranquil and sophisticated escape surrounded by natural beauty.

The Seven on Shelter hotel features a modern and minimalist design, blending seamlessly with the island’s serene atmosphere. The property is characterized by its sleek architecture, clean lines, and expansive windows that invite ample natural light and showcase the stunning surroundings.

The hotel offers a limited number of well-appointed guest rooms and suites that feature contemporary art and book collections in each room. Additional amenities include butter-soft cotton linens, flatscreen TVs, bath amenities from The Cold Spring Apothecary, and more.

A heated pool, croquet, bikes, yoga, and meditation add to this hotel’s charm and the hotel is pet friendly. 

Shelter Island House

Shelter Island House on Stearns Point Road is a historic property offers guests a unique blend of old-world charm and modern comfort, creating a delightful and inviting atmosphere.

The Shelter Island House hotel is housed in a beautifully restored Victorian mansion, which dates back to the 19th century. The building’s architectural details, including ornate woodwork, elegant balconies, and a wraparound porch, add to its timeless appeal and provide guests with a sense of the island’s rich history.

The hotel features a variety of stylish and cozy accommodations, catering to different preferences and group sizes. The rooms and suites are individually decorated with a mix of vintage and contemporary furnishings, creating a warm and welcoming ambiance. Each room is equipped with modern amenities such as flat-screen TVs, plush bedding, and private bathrooms, ensuring a comfortable stay for guests.

One of the highlights of Shelter Island House is its charming communal spaces. The hotel’s inviting common areas include a cozy living room with a fireplace, perfect for unwinding with a book or engaging in conversation with fellow guests. The spacious dining room offers a delightful setting for enjoying the hotel’s complimentary breakfast. The hotel also offers a voucher for a light breakfast at a nearby local bakery.

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