Shelter Island Heights, NY

Travel Guide

A pebbled beach with a sunset and a distant bridge.
A lake with houses on the shore, surrounded by trees and a clear sky.
A coastal landscape with a sunset, a marina, and a residential area.
A marina with numerous sailboats docked, a large tree in the foreground, and a flagpole with an American flag.
A calm lake reflecting trees and a clear sky.

Where to stay in Shelter Island Heights

Find the best Shelter Island Heights areas and neighborhoods for the activities you enjoy most.
A calm lake reflecting trees and a clear sky.
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.

A calm lake with reflections of clouds, surrounded by trees and a distant structure.

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

The Pridwin Hotel

4 out of 5
81 Shore Road Shelter Island Heights NY
The price is NT$28,813 per night from Jul 30 to Jul 31
NT$28,813
NT$36,211 total
Jul 30 - Jul 31
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! (93 reviews)
"The hotel itself, grounds rooms were beautiful, clean and very convenient and located. Views were beautiful from the oceanfront room that we had. The problem is with the food. The restaurant should be called the Mid wyn The breakfast was absolutely mediocre. The eggs were sitting there from 7 AM, ..."

Reviewed on 2026/7/15

The Pridwin Hotel
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
The price is NT$2,948 per night from Jul 23 to Jul 24
NT$2,948
NT$3,390 total
Jul 23 - Jul 24
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,000 reviews)
"Still the same wonderful little place as the last time I stayed here!"

Reviewed on 2026/7/11

Pier Blue Inn Old Saybrook - Essex
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 NT$40,235 per night from Aug 5 to Aug 6
NT$40,235
NT$55,162 total
Aug 5 - Aug 6
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! (825 reviews)
"-"

Reviewed on 2026/7/10

Gurney's Montauk Resort & Seawater Spa
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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

Montauk Manor

3.5 out of 5
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! (1,365 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 2026/7/9

Montauk Manor
North Fork Resort

North Fork Resort

3 out of 5
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' ...
9.4/10 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 2026/7/8

North Fork Resort
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
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! (271 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"

Reviewed on 2026/7/11

Cliffside Resort Condominiums
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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

Sunset Beach

9.4/10 (14 reviews)
Why not spend a carefree afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
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