Shelter Island Heights 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 Heights
Price found within the past 48 hours. Click for updated prices.
Life Hotel New York
Manhattan
Save 100% on your flight
Price was €1,741, price is now €1,191 per person
€1,191
per person
13 Dec - 18 Dec
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (1,258 reviews)
Room was clean, however hotel seems understaffed. Long wait for coffee service in the morning. Restaurant was fine, but forgettable.
Reviewed on 8 Nov 2025
Sofitel New York
Manhattan
Save 100% on your flight
Price was €2,516, price is now €1,745 per person
€1,745
per person
13 Dec - 18 Dec
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (1,175 reviews)
Should have trusted my gut to see reviews first. For a hotel with some status. $1k a night that doesn’t provide a kettle, coffee machine, bath room slippers. Has to be requested for. (And was told subject to availability and was lucky to have gotten it from the housekeeping staff) seriously? Friends also stayed in the suite, SUBPAR standard service etc for $2k a night. They are members and will have more to review.
Front service staff for checking in. Wow..leaves much to be desired. Make staff were just cordial and dead pan. Been to so many hotels and the price? This is really disappointing. Even a $200:night hotel at indigo NY gave better service and had EVERYTHING.
Saving grace? The Porters and doormen were exceptional along with the Housekeeping staff. THEY were the ones that gave 10/10 service.
Reviewed on 4 Nov 2025
Shelter Island Heights Beach Holiday
Escape the stresses of everyday life and let your body, mind and soul unwind on your Shelter Island Heights holiday. There's nothing more invigorating than the smell of salty sea air and the soothing melody of waves lapping at the shore. Plan your trip to Shelter Island Heights the easy way by choosing one of our Shelter Island Heights holiday packages. Many tourists choose to base themselves near Crescent Beach, a must-see just 2 kilometres from the downtown area.
Things You Should Know About Shelter Island Heights
- Check into one of our Shelter Island Heights beach hotels to appreciate the best this destination has to offer. Wander along the water's edge and be inspired by the stunning sunrises just moments from your front door.
- Alternatively, check out our range of private holiday homes. They're popular with travellers planning a stay in Shelter Island Heights. Consider Shelter Island House and The Chequit.
- There are tons of activities that keep the 1,050 or so residents of Shelter Island Heights occupied. Browsing our Shelter Island Heights things to do page will let you in on the best of what this place has to offer.
- Land great deals with a Shelter Island Heights holiday package. With the money you save, you won't regret indulging in this destination's best offerings. Sunset Beach, Crescent Beach and Crescent Beach are excellent places to start.
Top hotels in Shelter Island Heights
The Pridwin Hotel
81 Shore Road, Shelter Island Heights, NY
9.4/10 Exceptional! (83 reviews)
Overall the places is nice, clean and great views
Reviewed on 21 Oct 2025
The Chequit
23 Grand Ave, Shelter Island Heights, NY
8.8/10 Excellent! (37 reviews)
A cozy room with great pillows and quiet. Perfect little place.
Reviewed on 10 Oct 2025
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway, Montauk, NY
The price is €381 per night from 7 Dec to 8 Dec
€381
7 Dec - 8 Dec
includes taxes & fees
8.2/10 Very Good! (680 reviews)
Unbelievable stay! Staff was very accommodating. Beautiful views. Redone very nicely
Reviewed on 26 Oct 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.
Popular places to visit
Sylvester Manor
You can find out about the history of Shelter Island Heights when you stop by Sylvester Manor. Stroll along the beaches or discover the area's sunsets.
What to do in Shelter Island Heights
Long Island Wine and Food Day Trip with Sommelier host from NYC
€127
per adult
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
€153
per adult
76% of travellers recommend
More trip options
Expedia's Latest Trends
Hotels
Flights
Cars
Packages
Holiday Rentals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
