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 Wades 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 Wades Beach and Shelter Island Historical Society.

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$2,948 per night from Jul 22 to Jul 23
NT$2,948
NT$3,390 total
Jul 22 - Jul 23
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)
"Still the same wonderful little place as the last time I stayed here!"

Reviewed on 2026/7/11

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$36,212 per night from Jul 28 to Jul 29
NT$36,212
NT$49,646 total
Jul 28 - Jul 29
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 ...
8.4/10 Very Good! (825 reviews)
"-"

Reviewed on 2026/7/10

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is NT$14,919 per night from Jul 29 to Jul 30
NT$14,919
NT$17,675 total
Jul 29 - Jul 30
includes taxes & fees
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! (1,365 reviews)
"Rooms and facilty were clean and room was reasonably spacious. Comfortable bed. Nice kitchenette and balcony. Breakfast in b the restaurant was good. Outdoor pool very nice and heated. Close to most areas of interest. Shuttle available but we did not use."

Reviewed on 2026/7/9

Montauk Manor
See all 4,710 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! (1,365 reviews)
"Rooms and facilty were clean and room was reasonably spacious. Comfortable bed. Nice kitchenette and balcony. Breakfast in b the restaurant was good. Outdoor pool very nice and heated. Close to most areas of interest. Shuttle available but we did not use."

Reviewed on 2026/7/9

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' ...
9.4/10 Exceptional! (30 reviews)
"Overall the stay was pleasant. The cottages are well maintained. This property is still developing so there was active construction. It listed some amenities that were not yet available and some that were only available through a weekend stay which we did not have with a Sunday-Tuesday booking. I ..."

Reviewed on 2026/7/8

North Fork Resort
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
Book a stay at this beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...
9/10 Wonderful! (271 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"

Reviewed on 2026/7/11

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 carefree 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

A small boat with a canopy anchored near a dock.

Noyack