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
Menantic Creek
While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places 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 8.297.100 ₫ per night from 2 Dec to 3 Dec
8.297.100 ₫
11.324.357 ₫ total
2 Dec - 3 Dec
includes taxes & fees
8.2/10 Very Good! (685 reviews)
Well worth upgrading room. Amenities were amazing
Reviewed on 7 Nov 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
7.8/10 Good! (1,002 reviews)
The room was very clean with soft towels. The sheets were clean but a bit rougher than I'm used to (I like silky sheets, not rough cotton) but the bed was comfortable and warm. The staff is very friendly too. A nice "basic" room that took care of our needs, didn't gross me out with smell or dirt ...
Reviewed on 3 Nov 2025
Montauk Blue Hotel
108 South Emerson Avenue, Montauk, NY
9/10 Wonderful! (177 reviews)
Staff was nice beautiful news
Reviewed on 4 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
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.
