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The Latest Shelter Island Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Westin New York at Times Square
Manhattan
per person
30 Aug - 1 Sep
found 18 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
8.8/10 Excellent! (4,205 reviews)
It was so easy to get to broadway and Times Square. The subway was literally across the street too. The staff at front desk and luggage area couldn’t have been more helpful.
Reviewed on 6 Jun. 2024
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 Sunset Beach and Crescent Beach.
Our pick of the best Shelter Island Hotel Deals
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is NZ$147 per night from 9 Jun to 10 Jun
NZ$147
per night
9 Jun - 10 Jun
7.6/10 Good! (789 reviews)
"Most of these reviews give less than 5 stars because it’s outdated, which it is, but other than that I love my stay. I had no issues. Front desk staff were super friendly. Coffee machine in the room which was nice. Great area and location too, a lot of restaurants in walking distance. They are in ..."
Reviewed on 5 Jun. 2024
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is NZ$188 per night from 1 Jul to 2 Jul
NZ$188
per night
1 Jul - 2 Jul
7.4/10 Good! (966 reviews)
"Great hotel for the money, though it's a little off the beaten path (I had no idea where to find Old Saybrook from the hotel location). Still, it was perfect for my needs. They had a nice (free) continental breakfast and the pool area was great."
Reviewed on 28 May 2024
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway, Montauk, NY
The price is NZ$1,438 per night from 17 Jun to 18 Jun
NZ$1,438
per night
17 Jun - 18 Jun
8.2/10 Very Good! (570 reviews)
"Great time beautiful property"
Reviewed on 21 May 2024
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.
Frequently asked questions
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.
Shell Beach
Why not spend a care-free afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
Shelter Island Historical Society
You can enjoy some culture when you stop by Shelter Island Historical Society in Shelter Island. Stroll along the beaches or experience the area's museums.
What to do in Shelter Island
Private Hamptons Tour with Outlet Center Shopping
NZ$1,945
Per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.