Shelter Island Holidays
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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.
Shelter Island Beach Holiday
There's nothing like a Shelter Island holiday to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town centre on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometres away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.
Top hotels in Shelter Island
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
The price is €678 per night from 29 Apr to 30 Apr
€678
29 Apr - 30 Apr
includes taxes & fees
Montauk Manor
236 Edgemere St. Montauk NY
The price is €164 per night from 27 May to 28 May
€164
27 May - 28 May
includes taxes & fees
9.2/10 Wonderful! (1,333 reviews)
Everything is always excellent here. The rooms are always well stocked without being overstocked; you have the ability for physical and downloadable media to watch and enjoy; parking passes are always supplied without having to ask for them; wake up calls are attentive and they don't forget them; ...
Reviewed on 27 Apr 2026
Montauk Yacht Club
32 Star Island Rd Montauk NY
The price is €309 per night from 5 May to 6 May
€309
5 May - 6 May
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
The Montauk Yacht Club is a beautiful and relaxing getaway with a true coastal luxury feel. The property is well-maintained, with scenic waterfront views that make the entire experience feel special and refreshing. The rooms are comfortable and thoughtfully designed, offering a clean and modern aesthetic. ...
Reviewed on 21 Apr 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
