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 Sunset Beach and Shell Beach.
Top hotels in Shelter Island
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
The price is 9.971.010 ₫ per night from 1 Mar to 2 Mar
9.971.010 ₫
13.670.220 ₫ total
1 Mar - 2 Mar
includes taxes & fees
8.4/10 Very Good! (732 reviews)
The room was clean but was old and needed some updates and fixing. Staff were very friendly and courteous.
Reviewed on 24 Feb 2026
Montauk Manor
236 Edgemere St. Montauk NY
The price is 4.762.624 ₫ per night from 28 Feb to 1 Mar
4.762.624 ₫
5.951.846 ₫ total
28 Feb - 1 Mar
includes taxes & fees
9.2/10 Wonderful! (1,297 reviews)
Room was very nice
Reviewed on 17 Feb 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
8/10 Very Good! (1,000 reviews)
Very clean room. Staff was excellent. Very welcoming. Would and will stay there again, no question.
Reviewed on 22 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.
