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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is 2.115.761 ₫ per night from 28 Sept to 29 Sept
2.115.761 ₫
2.433.257 ₫ total
28 Sept - 29 Sept
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"Highly recommend!"
Reviewed on 21 Sept 2025
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway, Montauk, NY
The price is 12.381.562 ₫ per night from 28 Sept to 29 Sept
12.381.562 ₫
16.898.803 ₫ total
28 Sept - 29 Sept
includes taxes & fees
8.2/10 Very Good! (668 reviews)
"Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay."
Reviewed on 15 Sept 2025
Montauk Blue Hotel
108 South Emerson Avenue, Montauk, NY
The price is 3.936.133 ₫ per night from 26 Oct to 27 Oct
3.936.133 ₫
4.497.031 ₫ total
26 Oct - 27 Oct
includes taxes & fees
9/10 Wonderful! (142 reviews)
"Totally unobstructed view of a perfect sunrise over a perfect beach, absolutely sublime!"
Reviewed on 25 Sept 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.
