Shelter Island Travel Guide

Tourist Guide

A wooden gazebo by a pond with a large tree trunk nearby.
A sunset over a calm lake with a pier extending into the water, surrounded by trees and a road with a pedestrian crossing.
A large house with a dock extending into a calm body of water, surrounded by trees and other houses.
A gazebo on a rock by a river, surrounded by dense forest and a wooden fence.
A coastal landscape with a lake, dense greenery, and a sunset sky.

Where to stay in Shelter Island

Find the best Shelter Island areas for the activities you enjoy most. Learn more about Shelter Island
Learn more about Shelter Island
A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

A beach with a wooden sign that reads "Please take off your shoes!"

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Shelter Island Historical Society and Sunset Beach.

A pebble beach with calm water, a distant bridge, and a forested island.

Coecles Harbor

While Coecles Harbor isn't home to many top sights, Gardiner's Bay Country Club and Shelter Island Historical Society are some notable places to visit nearby.

A calm lake with reflections of clouds, surrounded by trees and a distant structure.

Hay Beach

When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.

An aerial view of a large estate surrounded by water, featuring a prominent mansion, rocky shorelines, and a small island with a lighthouse.

Shorewood

While Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Mashomack Preserve and Shelter Island Historical Society.

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
The price is 2.280.691 ₫ per night from 26 Aug to 27 Aug
2.280.691 ₫
2.622.795 ₫ total
26 Aug - 27 Aug
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8/10 Very good! (1,017 reviews)
"Needs to be updated badly. Would have spent more money to stay somewhere better."

Reviewed on 23 Aug 2026

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is 6.560.121 ₫ per night from 15 Sept to 16 Sept
6.560.121 ₫
9.736.760 ₫ total
15 Sept - 16 Sept
includes taxes & fees
Stay at this beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.4/10 Very good! (704 reviews)
"I was dissappointed to find out I had to pay for parking each night $25 was not told that would happen . charged me after the fact"

Reviewed on 25 Aug 2026

Sound View Greenport
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is 6.087.640 ₫ per night from 14 Sept to 15 Sept
6.087.640 ₫
7.451.418 ₫ total
14 Sept - 15 Sept
includes taxes & fees
Stay at this beach resort in Westbrook. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
Water's Edge Resort & Spa
See all 4,705 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
9.6/10 Exceptional! (50 reviews)
"THERE WAS ONLY ONE THING. THE LAST MORNING THERE WAS NO HOT H2O HOWEVER THE PROBLEM WAS FIXED."

Reviewed on 20 Aug 2026

North Fork Resort
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
Stay at this aparthotel in Montauk. Enjoy free Wi-Fi, an outdoor pool and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms in ...
9.2/10 Wonderful! (1,392 reviews)
"Beautiful property"

Reviewed on 25 Aug 2026

Montauk Manor
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
Stay at this beach aparthotel in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and East End ...
9/10 Wonderful! (288 reviews)
"Perfect"

Reviewed on 24 Aug 2026

Cliffside Resort Condominiums
See all properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Shelter Island attractions

A clear blue sea with a wooden pier extending into the water, a sailboat in the distance, and a person standing in the water.

Wades Beach

10.0/10 (1 review)
Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
See properties

Cities near Shelter Island

A sandy beach with wooden fences and houses on a dune.

East Hampton

An aerial view of a harbor with boats, a ship, and a dock extending into the water.

Greenport

A marina with several boats docked, including a white motorboat and a sailboat with a canopy.

Sag Harbor

A pebbled beach with a sunset and a distant bridge.

Shelter Island Heights

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