Shelter Island, NY

Travel 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 and neighborhoods for the activities you enjoy most.
A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

Silver Beach

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

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

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Shelter Island Historical Society and Sunset Beach.

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

Coecles Harbor

When in Coecles Harbor, you can plan a visit to Gardiner's Bay Country Club and Shelter Island Historical Society, some noteworthy sights in the nearby area.

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

Hay Beach

Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

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 there might not be top attractions in Shorewood, you can explore the larger area and discover places like Wades Beach and Mashomack Preserve.

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 NT$2,483 per night from Sep 28 to Sep 29
NT$2,483
NT$2,856 total
Sep 28 - Sep 29
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Pier Blue Inn Old Saybrook - Essex
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is NT$16,671 per night from Sep 29 to Sep 30
NT$16,671
NT$22,856 total
Sep 29 - Sep 30
includes taxes & fees
Book a stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Popular attractions Hither Woods Preserve and Hither ...
8.2/10 Very Good! (862 reviews)
"We stayed in the ocean front room. The room and view were beautiful. We had dinner at GIGIs. The food was good. The menu selection Was limited for us because we do not eat fish. The negative with Gurneys is the rooms are not connected to the main building. They do provide a car service to pick you ..."

Reviewed on 2026/9/25

Gurney's Montauk Resort & Seawater Spa
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
The price is NT$5,116 per night from Sep 28 to Sep 29
NT$5,116
NT$7,659 total
Sep 28 - Sep 29
includes taxes & fees
Stay at this hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Montauk Point Lighthouse and Montauk Point are located ...
Offshore Montauk
See all 4,622 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.
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
Stay at this aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
9.2/10 Wonderful! (1,407 reviews)
"The grounds are absolutely beautiful and well manicured. The shuttle service that the hotel offers is a wonderful and extremely helpful option! The staff was very kind and lovely especially Fiorella, Patrick, and Esteven!"

Reviewed on 2026/9/23

Montauk Manor
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
North Fork Resort
The Surf Club

The Surf Club

3.5 out of 5
20 Surfside Avenue Montauk NY
Book a stay at this beach aparthotel in Montauk. Enjoy free WiFi, a beach locale, and room service. Popular attractions Montauk Point Lighthouse and Bounce Beach ...
The Surf Club
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 close-up of a beach with various shells and pebbles.

Shell Beach

10.0/10 (1 review)
Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
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Cities near Shelter Island

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

East Hampton

A small boat with a canopy anchored near a dock.

Noyack