
Shelter Island Heights Holidays
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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! (67 reviews)
"Beautifully designed property with several unique and inviting spaces. Very comfortable room and bed and we took advantage of the complimentary use of the kayaks and paddle boards and easy access to the beach. The staff at the front desk and the pool bar were extremely friendly and laid back. Lovely ..."
Reviewed on 27 Jul 2025

The Chequit
23 Grand Ave, Shelter Island Heights, NY
8.8/10 Excellent! (32 reviews)
"we loved it!"
Reviewed on 9 Jul 2025

Marram
21 Oceanview Terrace, Montauk, NY
The price is €486 per night from 2 Sept to 3 Sept
€486
2 Sept - 3 Sept
includes taxes & fees
8.6/10 Excellent! (198 reviews)
"Amazing atmosphere. Relaxing yet family friendly. Everything was clean and we felt safe and the staff was helpful"
Reviewed on 1 Aug 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
€137
per adult

From Mattituck: North Fork Area Bike Tour with Food Tasting
€120
per adult
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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.