Shelter Island Holidays
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Our guide on 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 Crescent Beach and Sunset Beach.
Shelter Island Holiday
Our pick of the best Shelter Island Hotel Deals
Montauk Yacht Club
32 Star Island Rd, Montauk, NY
The price is NZ$499 per night from 4 May to 5 May
NZ$499
includes taxes & fees
4 May - 5 May
8.4/10 Very Good! (999 reviews)
"The staff was kind and very hospitable. Very beautiful environment and clean place to stay."
Reviewed on 29 Apr. 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is NZ$172 per night from 5 May to 6 May
NZ$172
includes taxes & fees
5 May - 6 May
7.6/10 Good! (952 reviews)
"The owner was so helpful and friendly. When our car wouldn't start due to a dead battery, he called a friend to drive over to give us a jump (since the owner's car was a hybrid and he couldn't access his battery). The grounds are beautifully landscaped with lots of blooming trees and flowers. It's ..."
Reviewed on 28 Apr. 2025
Water's Edge Resort & Spa
1525 Boston Post Road, Westbrook, CT
Fully refundableReserve now, pay when you stay
The price is NZ$407 per night from 4 May to 5 May
NZ$407
includes taxes & fees
4 May - 5 May
8.6/10 Excellent! (1,001 reviews)
"Spa was fantastic, rooms are nothing extravagant but clean and well maintained. Everyone was polite, great stay"
Reviewed on 29 Apr. 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.
Discover the most popular places to visit in Shelter Island
Gardiner's Bay Country Club
Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.
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.
Wades Beach
Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.