Shelter Island Heights Travel Guide
Tourist Guide
Visit Shelter Island Heights
Where to stay in Shelter Island Heights
Find the best Shelter Island Heights areas 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
When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.
The Pridwin Hotel
81 Shore Road Shelter Island Heights NY
The price is ฿23,501 per night from 11 Aug to 12 Aug
฿23,501
฿29,534 total
11 Aug - 12 Aug
includes taxes & fees
Stay at this beach hotel in Shelter Island Heights. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
9.6/10 Exceptional! (91 reviews)
"We had such an amazing time at the Pridwin! The hotel is gorgeous and everything is kept clean and organized for guests!"
Reviewed on 5 Jul 2026
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
The price is ฿34,125 per night from 26 Jul to 27 Jul
฿34,125
฿46,786 total
26 Jul - 27 Jul
includes taxes & fees
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 Hills ...
8.4/10 Very good! (820 reviews)
"-"
Reviewed on 10 Jul 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is ฿2,851 per night from 13 Jul to 14 Jul
฿2,851
฿3,279 total
13 Jul - 14 Jul
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8/10 Very good! (1,015 reviews)
"Still the same wonderful little place as the last time I stayed here!"
Reviewed on 11 Jul 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 Wi-Fi, an outdoor pool and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms in ...
9.2/10 Wonderful! (1,365 reviews)
"Rooms and facilty were clean and room was reasonably spacious. Comfortable bed. Nice kitchenette and balcony. Breakfast in b the restaurant was good. Outdoor pool very nice and heated. Close to most areas of interest. Shuttle available but we did not use."
Reviewed on 9 Jul 2026
North Fork Resort
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
9.4/10 Exceptional! (30 reviews)
"Overall the stay was pleasant. The cottages are well maintained. This property is still developing so there was active construction. It listed some amenities that were not yet available and some that were only available through a weekend stay which we did not have with a Sunday-Tuesday booking. I ..."
Reviewed on 8 Jul 2026
Cliffside Resort Condominiums
61475 Route 48 (North Road) Greenport NY
Stay at this beach aparthotel in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and East End ...
9/10 Wonderful! (269 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
Reviewed on 11 Jul 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.
Stay near popular Shelter Island Heights attractions
Things to do
Private Luxury Wine Tours of Long Island Pindar Winery
฿5,913
per adult
Half Day(PM) North Fork Private Wine & Food Tour by Local Expert
฿11,136
per adult
Private Vacation Photoshoot with Photographer The Hamptons
฿9,283
per adult
