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

The Pridwin Hotel

4 out of 5
81 Shore Road Shelter Island Heights NY
The price is S$1,003 per night from 28 Jun to 29 Jun
S$1,003
28 Jun - 29 Jun
includes taxes & fees
9.6/10 Exceptional! (88 reviews)
"Beautiful! Relaxing vacation! A bit pricey, to be expected. Barbecue ($85) was beautifully set up. Menu was disappointing. Past reviews cited appetizers like lobster rolls and fritto misto. These were absent. $4 for a small lemonade which was mostly ice, REALLY!"

Reviewed on 19 Jun, 2026

The Pridwin Hotel
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is S$1,809 per night from 30 Jun to 1 Jul
S$1,809
30 Jun - 1 Jul
includes taxes & fees
8.4/10 Very good! (811 reviews)
"Amazing stay over Father's Day weekend. Weather was perfect. Staff was very helpful and friendly from the valet, to reception, to the breakfast cafe, to the spa and beach staff. Bicycles were readily available as well. Our only unexpected minor irritation was the extremely loud outdoor music until ..."

Reviewed on 23 Jun, 2026

Gurney's Montauk Resort & Seawater Spa
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
The price is S$1,114 per night from 20 Jul to 21 Jul
S$1,114
20 Jul - 21 Jul
includes taxes & fees
9.2/10 Wonderful! (142 reviews)
"It was a comfortable room and well-located."

Reviewed on 23 Jun, 2026

Offshore Montauk
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.