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 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 Wades Beach 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 Sunset Beach 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 Wades Beach and Sunset 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 S$1,905 per night from 8 Jul to 9 Jul
S$1,905
8 Jul - 9 Jul
includes taxes & fees
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 Hills ...
8.4/10 Very good! (817 reviews)
"Beautiful room and location!"

Reviewed on 1 Jul, 2026

Gurney's Montauk Resort & Seawater Spa
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
The price is S$941 per night from 20 Jul to 21 Jul
S$941
20 Jul - 21 Jul
includes taxes & fees
Stay at this hotel in Montauk. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Montauk Point Lighthouse and Montauk Point are located ...
9.2/10 Wonderful! (146 reviews)
"Amazing location to the beach and town. Brand new. All the appliances and amenities were great. The pool area great as well. Currently building a bar/ resturaunt at the pool to be open for next summer Wouldn’t stay anywhere else in Montauk"

Reviewed on 30 Jun, 2026

Offshore Montauk
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 S$133 per night from 9 Jul to 10 Jul
S$133
9 Jul - 10 Jul
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! (1,004 reviews)
"Good price for a nite in area..lovely front desk woman at check in and check out Room on ground floor smelled a bit musty and this am discovered only one coffee cup for 2 people...no biggie as there is the deightful & yummy Tea Kettle right across the street. Amazing breakfast choices & very friendly ..."

Reviewed on 3 Jul, 2026

Pier Blue Inn Old Saybrook - Essex
See all 4,741 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 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! (1,362 reviews)
"Property and room very clean Friendly staff and plenty of parking"

Reviewed on 3 Jul, 2026

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 Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
9.2/10 Wonderful! (25 reviews)
"We loved our stay at the North Fork Resort. We would definitely recommend. Family & pet friendly to the max! Any hiccups we had with our stay were resolved without hesitation or annoyance by the staff. They were incredibly accommodating. The pool area was spacious and clean but the pool itself was ..."

Reviewed on 26 Jun, 2026

North Fork Resort
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! (266 reviews)
"Clean condo with everything you need. Pool, rocky beach and plenty of parking. Close to all, loved our stay. AC was excellent too!"

Reviewed on 3 Jul, 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
A sandy beach with wooden fences and houses on a dune.

East Hampton

A calm lake with a forest in the background during sunset.

Southold

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