Shelter Island Heights
Travel Guide
Visit Shelter Island Heights
Where to stay in Shelter Island Heights
Find the best Shelter Island Heights areas and neighborhoods for the activities you enjoy most.
Photo by Erisa Dilo
Open Photo by Erisa Dilo
The Heights
If you're spending some time in The Heights, Sunset Beach and Shelter Island Country Club are top sights worth seeing.
Hay Beach
Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.
The Pridwin Hotel
81 Shore Road Shelter Island Heights NY
The price is CA $792 per night from Jun 16 to Jun 17
CA $792
CA $995 total
Jun 16 - Jun 17
includes taxes & fees
Book a stay at this beach hotel in Shelter Island Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.6/10 Exceptional! (87 reviews)
"We had an absolutely enchanting long weekend at the Pridwin. This beautifully appointed property exudes timeless elegance, with thoughtful touches that made us feel truly pampered from the moment the staff reached out to us long before our stay. The complimentary breakfast, in-room snacks and drinks, ..."
Reviewed on Jun 8, 2026
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
The price is CA $1,411 per night from Jul 12 to Jul 13
CA $1,411
CA $1,934 total
Jul 12 - Jul 13
includes taxes & fees
Book a stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Popular attractions Hither Woods Preserve and Hither ...
8.4/10 Very Good! (794 reviews)
"Great location, excellent facilities. Staff very mixed - some incredible and some terrible. Cumulative number of issues but dealt with by a member of the management team after getting fed up of a number of things, Including: Dog mess left for > 24 hours after reporting it. Staff member laughed and ..."
Reviewed on Jun 9, 2026
Offshore Montauk
71 S Emerson Ave Montauk NY
The price is CA $795 per night from Jun 14 to Jun 15
CA $795
CA $1,068 total
Jun 14 - Jun 15
includes taxes & fees
Stay at this hotel in Montauk. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Montauk Point and Kirk Park Beach are located ...
9.4/10 Exceptional! (135 reviews)
"Great experience!"
Reviewed on May 30, 2026
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.
Montauk Manor
236 Edgemere St. Montauk NY
Stay at this aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
9.2/10 Wonderful! (1,357 reviews)
"all beautiful"
Reviewed on Jun 2, 2026
North Fork Resort
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
9.2/10 Wonderful! (22 reviews)
"Very nice place, overall. New and new construction nearby (dust); they’re still ironing-out some kinks, but cute cottages, clean, nicely styled and furnished with great outdoor amenities. Staff are friendly and welcoming, but still getting into a groove. Once the final details are squared-away, will ..."
Reviewed on Jun 8, 2026
Cliffside Resort Condominiums
61475 Route 48 (North Road) Greenport NY
Book a stay at this beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...
9/10 Wonderful! (256 reviews)
"Beautiful, clean condo..gorgeous view"
Reviewed on Jun 12, 2026
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.
