Rental Car
Set between the North and South forks of Long Island, Shelter Island is a tiny island 90 miles from Manhattan on the eastern end of Long Island. Guests may take the South Ferry from North Haven/Sag Harbor, or the North Ferry from Greenport. Reservations for the ferry are not necessary as the ferry runs every 10 minutes to the island. Tickets are less than $20 with a car, cash only. TIP: Driving North on the LIE to Greenport is generally faster because you avoid Hamptons traffic, but check google maps when you depart for the quickest route.
Flight
Guests should book travel/flights to arrive to Islip, John F. Kennedy or LaGuardia. TIP: Long Island MacGarthur/Islip airport is 55 miles west of Shelter Island, however the only airlines that fly into MacGarthur/Islip are American, Frontier and southwest.
Train
Take the Long Island Railroad from Penn Station to Ronkonkoma, then transfer in Ronkonkoma to Greenport. From Greenport, you can walk to the North Ferry to get to Shelter Island. Passengers without cars can purchase $2 tokens, cash only.
House Or Rental
Want to get a group together for the weekend? There are some great options all around Shelter Island to choose from.
Hotel
Drawing inspiration from its original roots in the 1800s, Shelter Island House has been reinvented with luxurious modern beach flair and opulent accommodations. Style, distinction, warmth, and intimacy are combined with architecture that has maintained its historic details and chic elegance.
Hotel
A Gasby Era Hotel -- The Pridwin Hotel and Cottages is a classic all-wood American resort hotel that has been providing guests a unique experience on Shelter Island since 1927. The nearly 10-acre site on Crescent Beach was selected for its protected waters, gentle bay breezes, and for its breathtaking water views.
Hotel
The Chequit is located in Shelter Island Heights with many charming spaces. Guests can stay in the 31 guestrooms in the Main House and Cottage or in the six-bedroom Summer House.
Hotel
A 181 year old Victorian, situated on 1.5 acres in the center of Shelter Island. Recently redecorated, The Candlelite Inn has 5 guest rooms with private baths, central air conditioning, television in the common living room and offers a continental breakfast.
Hotel
Located on Crescent Beach with gorgeous sunset views.
Hotel
A European-inspired B&B includes farm fresh organic eggs, local granola + honey, pain au chocolate and warmed baguettes served with sweet butter, local preserves and tasty cheeses. A short walk to the lively Sunset Beach restaurant & bar and Crescent Beach and Goat Hill golf course.
Hotel
The once family home has been converted to a beautifully appointed guest house. This Shelter Island inn is conveniently located within walking distance to Crescent beach, shops, restaurants and activities. Each room has it’s own unique sweetness with luxurious king size beds, private contemporary baths and chic beach furnishings. Intimate and thoughtful for your perfect summer escape.
Hotel
This B&B located on a quiet lane overlooking an inlet. The rooms are furnished with antiques and there are yellow pine floors throughout. Three guest rooms are located on the second floor. The suite is on the first floor and comprises an adjoining sitting room with a cozy fireplace and a small outside patio. All rooms have private bathrooms. A light continental breakfast is served daily in the sun room and, with its panoramic view of Chase Creek.