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 marina with numerous sailboats docked, a large tree in the foreground, and a flagpole with an American flag.
A coastal landscape with a sunset, a marina, and a residential area.
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.

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 Chequit

The Chequit

3 out of 5
23 Grand Ave Shelter Island Heights NY
The price is ₩240,628 per night from Nov 16 to Nov 17
₩240,628
₩274,918 total
Nov 16 - Nov 17
includes taxes & fees
Stay at this hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Shelter Island Country Club and Sunset ...
9/10 Wonderful! (78 reviews)
"We went for a nice weekend getaway and we were not disappointed. The room was really nice, the coffee shop was perfect for a morning latte and cup of coffee. We went to the bar and restaurant both days and the staff were absolutely amazing and professional and provided quality service. The food and ..."

Reviewed on Nov 8, 2026

The Chequit
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 ₩486,602 per night from Nov 29 to Nov 30
₩486,602
₩667,127 total
Nov 29 - Nov 30
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 ...
8.2/10 Very Good! (881 reviews)
"Perfect"

Reviewed on Nov 14, 2026

Gurney's Montauk Resort & Seawater Spa
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 ₩103,692 per night from Nov 16 to Nov 17
₩103,692
₩119,246 total
Nov 16 - Nov 17
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. ...
Pier Blue Inn Old Saybrook - Essex
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 ...
Montauk Manor
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway Amagansett NY
Book a stay at this beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Windward Shores Ocean Resort
Montauk Oceanside Suites

Montauk Oceanside Suites

3 out of 5
115 South Emerson Avenue Montauk NY
Stay at this aparthotel in Montauk. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Montauk Point Lighthouse and Montauk Point are ...
Montauk Oceanside Suites
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