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 2.111.997 ₫ per night from 8 Oct to 9 Oct
2.111.997 ₫
2.428.928 ₫ total
8 Oct - 9 Oct
includes taxes & fees
7.8/10 Good! (1,005 reviews)
"For a budget hotel its not bad - area is generally pricy - its just needs a facelift - it needs to remove the carpets. Staff is nice."
Reviewed on 4 Oct 2025
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway, Montauk, NY
The price is 8.206.729 ₫ per night from 30 Oct to 31 Oct
8.206.729 ₫
11.200.965 ₫ total
30 Oct - 31 Oct
includes taxes & fees
8.2/10 Very Good! (669 reviews)
"wonderful place only criticism is how far away rooms are from lobby and the rest of the facilities"
Reviewed on 29 Sept 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is 2.465.315 ₫ per night from 2 Nov to 3 Nov
2.465.315 ₫
2.835.112 ₫ total
2 Nov - 3 Nov
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"Overall, a nice hotel for a one day trip! :)"
Reviewed on 5 Oct 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.
