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 Crescent Beach.
Top hotels in Shelter Island
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
The price is 16.456.875 ₫ per night from 3 May to 4 May
16.456.875 ₫
22.562.244 ₫ total
3 May - 4 May
includes taxes & fees
8.4/10 Very Good! (753 reviews)
WE HAD A LOVELY WEEKEND. SERVICE WAS EXCELLENT.
Reviewed on 6 Apr 2026
Montauk Manor
236 Edgemere St. Montauk NY
The price is 3.980.491 ₫ per night from 11 May to 12 May
3.980.491 ₫
5.063.543 ₫ total
11 May - 12 May
includes taxes & fees
9.2/10 Wonderful! (1,320 reviews)
Excellent experience. This is traditional “attention to detail” and “above and beyond” at its best.
Reviewed on 11 Apr 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is 6.265.113 ₫ per night from 19 Apr to 20 Apr
6.265.113 ₫
7.659.089 ₫ total
19 Apr - 20 Apr
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
it was our first time and we really enjoyed the place. The Band was amazing! Being at the resort made our weekend great. Will definitely be back!
Reviewed on 11 Apr 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
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.
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.
