Shelter Island

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. 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 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 Shell 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 Mashomack Preserve, some noteworthy sights in the nearby area.
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 Wades Beach and Shelter Island Historical Society.
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 Shell Beach.
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 CA $520 per night from Nov 16 to Nov 17
CA $520
CA $713 total
Nov 16 - Nov 17
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! (875 reviews)
"Restaurant was excellent . Rooms needed repairs and resort fee should have been waived for broke room items"

Reviewed on Oct 26, 2026

Gurney's Montauk Resort & Seawater Spa
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is CA $251 per night from Nov 1 to Nov 2
CA $251
CA $313 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Water's Edge Resort & Spa
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 CA $115 per night from Nov 15 to Nov 16
CA $115
CA $132 total
Nov 15 - Nov 16
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. ...
8/10 Very good! (1,000 reviews)
"The room had a musty smell when we entered and didn't resemble in the least how it was presented on the website. The room looked dirty, pillows looked old and stained yellow. The television didn't work. The shower barely had any pressure. The employees were very nice."

Reviewed on Oct 27, 2026

Pier Blue Inn Old Saybrook - Essex
See all 4,610 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 ...
Montauk Manor
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway Amagansett NY
Book a stay at this beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Windward Shores Ocean Resort
Montauk Oceanside Suites

Montauk Oceanside Suites

3 out of 5
115 South Emerson Avenue Montauk NY
Stay at this aparthotel in Montauk. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Montauk Point Lighthouse and Montauk Point are ...
8.6/10 Excellent! (457 reviews)
"Really loved the location of this lodging. We were within walking distance to the town and to the beach."

Reviewed on Oct 19, 2026

Montauk Oceanside Suites
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.
See properties

Cities near Shelter Island

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

East Hampton

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

Sag Harbor

A coastal landscape with a sandy beach, calm water, and scattered trees.

East Marion

A coastal landscape with a sandy beach, clear blue water, and a distant lighthouse.

Greenport West

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