Shelter Island Holidays
Photo by Brian V. Rowe
- Plan, book, travel with confidence
- Better togetherSave up to €185 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Shelter Island
Price found within the past 48 hours. Click for updated prices.
Lotte New York Palace
Manhattan
Save 100% on your flight
Price was €1,483, price is now €973 per person
€973
per person
28 Jan - 1 Feb
found 14 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,723 reviews)
Beautiful hotel, great rooms, bed very comfortable, amazing costumer service and great for Christmas time!
Reviewed on 24 Dec 2025
The Fifth Avenue Hotel
Manhattan
Save 100% on your flight
Price was €4,597, price is now €2,565 per person
€2,565
per person
14 Mar - 21 Mar
found 15 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9.6/10 Exceptional! (159 reviews)
We had a great stay. Room was comfortable and had what we needed. The staff was professional and some were exceptional. Our room attendant, Nini, stood out as making our stay memorable with her professional work ethic and kindness. Would stay here again. Also enjoyed the restaurant
Reviewed on 13 Dec 2025
Hotel Riu Plaza New York Times Square
Manhattan
Save 100% on your flight
Price was €3,401, price is now €2,037 per person
€2,037
per person
1 Mar - 6 Mar
found 24 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (2,790 reviews)
Clean rooms, grab and go food options, Breakfast included. Fast Elevators. However car 2 doesn't work most of the time.
Reviewed on 24 Dec 2025
Hotel Seville Nomad, in the Unbound Collection by Hyatt
Manhattan
Price was €1,540, price is now €1,010 per person
€1,010
per person
15 Mar - 20 Mar
found 22 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (1,184 reviews)
No glasses in the room - forcing to buy water?
Reviewed on 23 Dec 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
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 €477 per night from 15 Jan to 16 Jan
€477
15 Jan - 16 Jan 2026
includes taxes & fees
8.2/10 Very Good! (704 reviews)
Everything was perfect. Staff, room, experience. Will definitely stay again.
Reviewed on 14 Dec 2025
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is €238 per night from 5 Jan to 6 Jan
€238
5 Jan - 6 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Everything was wonderful. Staff was friendly, very clean,we enjoyed it.
Reviewed on 20 Dec 2025
Montauk Blue Hotel
108 South Emerson Avenue Montauk NY
9.2/10 Wonderful! (187 reviews)
I always have a 5/5 stay at Montauk Blue.
Reviewed on 19 Nov 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
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
€154
per adult
76% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
