Shelter Island Holidays
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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
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.
Top hotels in Shelter Island
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
The price is 7.596.225 ₫ per night from 22 Feb to 23 Feb
7.596.225 ₫
10.414.522 ₫ total
22 Feb - 23 Feb
includes taxes & fees
8.2/10 Very Good! (724 reviews)
Room was spotless, staff were great and the resort is top notch!!
Reviewed on 2 Feb 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is 3.835.398 ₫ per night from 4 Mar to 5 Mar
3.835.398 ₫
5.123.645 ₫ total
4 Mar - 5 Mar
includes taxes & fees
8.4/10 Very Good! (612 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...
Reviewed on 10 Jan 2026
Montauk Manor
236 Edgemere St. Montauk NY
The price is 3.599.442 ₫ per night from 19 Feb to 20 Feb
3.599.442 ₫
4.620.583 ₫ total
19 Feb - 20 Feb
includes taxes & fees
9/10 Wonderful! (1,294 reviews)
Love this place
Reviewed on 12 Feb 2026
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.
Popular places to visit
Mashomack Preserve
Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.
Shelter Island Historical Society
You can spend time browsing the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.
