Shelter Island Holidays
Photo by Brian V. Rowe
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Top Flight + Hotel Deals in Shelter Island
Price found within the past 48 hours. Click for updated prices.
Romer Hell's Kitchen
Manhattan
Price was €1,540, price is now €1,035 per person
€1,035
per person
22 Oct - 28 Oct
found 24 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.4/10 Exceptional! (2,040 reviews)
We loved our stay at Romer Hell’s Kitchen! Centrally located to move around the city with ease. We will definitely go back!!
Reviewed on 21 Sept 2025
Hotel Riu Plaza New York Times Square
Manhattan
Price was €2,316, price is now €1,408 per person
€1,408
per person
8 Dec - 12 Dec
found 13 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (2,730 reviews)
Booked this hotel for my birthday and had a wonderful experience! They let me check in early which I was so glad for after long travels, the room was clean the view was breathtaking, the staff we very accommodating, the breakfast was immaculate. Definitely recommend!!
Reviewed on 21 Sept 2025
Distrikt Hotel New York City, Tapestry Collection by Hilton
Manhattan
Save 100% on your flight
Price was €1,876, price is now €1,219 per person
€1,219
per person
4 Dec - 9 Dec
found 15 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
8.2/10 Very Good! (1,008 reviews)
Staff were really fun - everyone had such a positive attitude. Very grateful for their cheery dispositions
Reviewed on 21 Sept 2025
Hyatt Centric Times Square New York
Manhattan
Save 100% on your flight
Price was €1,576, price is now €1,041 per person
€1,041
per person
30 Oct - 3 Nov
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (1,866 reviews)
Clean, great staff, surprisingly quiet
Reviewed on 18 Sept 2025
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.
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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is €78 per night from 23 Sept to 24 Sept
€78
23 Sept - 24 Sept
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"We were in town for a party. Very convenient location and friendly staff."
Reviewed on 14 Sept 2025
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway, Montauk, NY
The price is €545 per night from 28 Sept to 29 Sept
€545
28 Sept - 29 Sept
includes taxes & fees
8.2/10 Very Good! (667 reviews)
"Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay."
Reviewed on 15 Sept 2025
Montauk Blue Hotel
108 South Emerson Avenue, Montauk, NY
The price is €155 per night from 19 Oct to 20 Oct
€155
19 Oct - 20 Oct
includes taxes & fees
9/10 Wonderful! (134 reviews)
Really good older hotel with a great view.
"This was an older hotel but right on the water with a great ocean view. Good spacious room with couch, table and chairs, a small fridge, and a coffeemaker. The desk staff were very friendly and helpful with directions and restaurant suggestions. Two small issues. The toilet is ridiculously small ..."
Reviewed on 13 Sept 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.
What to do in Shelter Island
From Mattituck: North Fork Area Bike Tour with Food Tasting
€118
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
