The quiet charm of Shelter Island

Nestled in-between the North and South Forks of Long Island, Shelter Island can be reached via a short ferry ride and yet it
feels miles away from it’s Hamptons and Wine Country neighbors.  A charming waterfront community with a personality all its own.

Where to Stay

Accommodations in Shelter Island range from small boutique hotels to home rentals that can accommodate groups and families.

The Chequit Inn

Initially built in 1872 and renovated in 2015, this boutique hotel has been reimagined using a refreshing light pastel palette, along with modern touches like updated bathrooms and luxury bedding. Some rooms can be combined to accommodate families. Your stay includes a rustic breakfast or "Breakfast in Bed" delivered to your room. Evening drinks served in the lobby from 4-9pm and the on-site restaurant, Red Maple, features local and seasonal cuisine in a rustic atmosphere. For a morning pick me up, stop by the White Hill Cafe where you can grab your morning coffee or pick up supplies for your beach picnic.

Shelter Island House

Quaint boutique hotel with chic rooms, pool, and access to bikes to explore the Island. Bocce ball court and lots of cozy nooks to relax and enjoy the scenery. On-site dining and bakery.

The Clinton Avenue Cottage

Restored waterfront Victorian cottage with gingerbread trim sleeps 8 and is ideally situated in Shelter Island Heights. A 5-minute walk to the North Ferry, private beach club, tennis courts, restaurants, and shops, the cottage is perfect for families with young children or for an extended family gathering. The formal dining room and spacious kitchen provide a comfortable space for preparing and enjoying meals together. - Kid & Coe

Luxury Shelter Island Complex

This stylish home has three floors of living space, a wraparound deck, and guest house. Living area with towering cathedral ceilings, a modern chef’s kitchen, large pool, movie theater, kids playroom, built-in BBQ area, and private garden. Short walk to Sunset beach. With 8 Bedrooms and 7 Bathrooms, this home can accommodate up to 14 guests.

Where to Eat

For a small island, Shelter Island has several excellent fine-dining and casual dining options.

18 Bay Restaurant

A charming restaurant in a historical Shelter Island farmhouse features a set menu that changes weekly based on what is currently in season. The casual and welcoming atmosphere gives way to elevated dining and attention to detail that allows the chef/owners to showcase their skills. The Italian inspired menu includes four-course antipasti using local produce, seafood, and meat, followed by a homemade pasta course and then your choice of two entrees. House-made desserts complete the dining experience. The wine list focuses on small producers that have been curated to complement the menu.
23 North Ferry Rd (Rt 114), Shelter Island, NY

Marie Eiffel Market

Trained in Paris, Marie Eiffel Market is a specialty-foods market offering organic fare, french inspired cuisine, local produce, and premium groceries. Line up early to get the pain au chocolate and feel transported to your favorite patisserie in Paris. The real treat is taking your food out through the back of the market and enjoying it on the small dock overlooking Dering Harbor.
184 N. Ferry Road, Shelter Island, NY 11965

Vine Street Cafe

Relaxed and sophisticated but not fussy, the Vine Street Cafe features locally sourced and seasonally influenced food prepared by Terry Harwood. Terry, along with his wife, Lisa Murphy Harwood opened the Vine Street Cafe in 2003 after stints at established restaurants across the country, like the Union Square Cafe in NY and Jardinière in San Fransisco. Nightly specials are consistent from week to week and include stand-outs like Bouillabaisse.
41 South Ferry Road, Shelter Island, NY

Sunset Beach

If you are looking for a scene, check out Sunset Beach - you will find it there.  With a European feel and a festive vibe you can enjoy the coastal Mediterranean fare with a view of Crescent Beach, this hotspot has a lively scene and fire pit. The menu includes a wine list that trends on the expensive side for what it is.
35 Shore Road, Shelter Island Heights, NY

What to Do

Beaches

Wades Beach on the south side of the island, has lifeguards and restrooms making, this is a popular spot for families. Crescent Beach (AKA Sunset Beach) is the spot on the island to catch the sunset. On the other side of the island from Crescent is Shell Beach, a narrow beach about three-quarters of a mile in length that protrudes into Shelter Island Sound. Accessible only by a narrow, unpaved road, Shell beach has no amenities. Lifeguards are on duty from 10 a.m. to 5 p.m. at both Wades and Crescent. Visitors may purchase permits for $35 per week, $75 per month or $200 for the season with the Town Clerk.

Shop

Bright and preppy, shop Dabney Lee for cheeky pool floats, festive party decor, and fun office supplies. You’ll be sure to find something to brighten your day or find a great hostess gift. If you are looking for a good book to curl up with, Finley’s Fiction in Shelter Island Heights is located across from the Chequit Inn. The book store is a family run operation and has all genres of books inclusive of a curated section for kids. Sylvester Manor Farm Stand is an excellent place for the kids to run around and pick out the fresh produce.

For the Kids