Shelter Island Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Brian V. Rowe
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 7.096.607 ₫ per night from 2 Feb to 3 Feb
7.096.607 ₫
9.729.524 ₫ total
2 Feb - 3 Feb
includes taxes & fees
8.2/10 Very Good! (712 reviews)
The Spa was Amazing! I didn't have breakfast.
Reviewed on 5 Jan 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is 6.015.830 ₫ per night from 8 Feb to 9 Feb
6.015.830 ₫
7.371.362 ₫ total
8 Feb - 9 Feb
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
Great place!
Reviewed on 31 Dec 2025
Montauk Blue Hotel
108 South Emerson Avenue Montauk NY
9.2/10 Wonderful! (187 reviews)
I always have a 5/5 stay at Montauk Blue.
Reviewed on 19 Nov 2025
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.
