Shelter Island Holidays
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Top Flight + Hotel Deals in Shelter Island
Price found within the past 48 hours. Click for updated prices.
Sheraton New York Times Square Hotel
Manhattan
Price was €719, price is now €453 per person
€453
per person
10 Jun - 13 Jun
found 1 day ago
Return flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (7,617 reviews)
Room had hair everywhere.. STAFF WAS RUDE WHEN I asked about transportation back to the airport very rude.
Reviewed on 28 Apr 2026
Hotel Riu Plaza New York Times Square
Manhattan
Price was €1,117, price is now €658 per person
€658
per person
10 Jun - 13 Jun
found 1 day ago
Return flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,950 reviews)
The buffet breakfast was the highlight of our stay. Absolutely exceptional. Very plentiful with a wide selection of both hot and cold items, beautiful dining room. Highly recommended.
Reviewed on 27 Apr 2026
1 Hotel Brooklyn Bridge
Price was €3,367, price is now €2,051 per person
€2,051
per person
6 Jun - 9 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
Don’t ever think you will check in prior to the late 4pm check in. No matter what. Not even 5 minutes.
Reviewed on 17 Apr 2026
42 Hotel
Save 100% on your flight
Price was €1,976, price is now €1,251 per person
€1,251
per person
1 Jun - 8 Jun
found 21 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (858 reviews)
This Hotel is so cool. The staff is beyond helpful and friendly. We cant wait to come back next year.
Reviewed on 15 Apr 2026
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 €737 per night from 12 May to 13 May
€737
12 May - 13 May
includes taxes & fees
Montauk Manor
236 Edgemere St. Montauk NY
The price is €164 per night from 26 May to 27 May
€164
26 May - 27 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 4 May to 5 May
€309
4 May - 5 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.
