Shelter Island Heights Travel Guide

Tourist 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 for the activities you enjoy most. Learn more about Shelter Island Heights
Learn more about Shelter Island Heights
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

When in Hay Beach, you can plan a visit to Greenport Carousel and Greenport Harbor Brewing Company, some noteworthy sights in the nearby area.

The Chequit

The Chequit

3 out of 5
23 Grand Ave Shelter Island Heights NY
The price is 5.382.621 ₫ per night from 6 Oct to 7 Oct
5.382.621 ₫
6.149.645 ₫ total
6 Oct - 7 Oct
includes taxes & fees
Stay at this hotel in Shelter Island Heights. Enjoy free Wi-Fi, free parking and premium bedding. Popular attractions Shelter Island Country Club and Sunset ...
9.2/10 Wonderful! (59 reviews)
"Amazing!! staff were lovely and hotel is so clean and so pretty"

Reviewed on 16 Sept 2026

The Chequit
The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road Shelter Island Heights NY
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. ...
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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 2.121.585 ₫ per night from 22 Sept to 23 Sept
2.121.585 ₫
2.439.862 ₫ total
22 Sept - 23 Sept
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! (1,003 reviews)
"Staff was helpful and professional. Room was clean, basic, nice. The TV was a little sketchy-some stations were static. The bathroom shower was great: good flow, hot and soothing. Overall, very good for the price."

Reviewed on 17 Sept 2026

Pier Blue Inn Old Saybrook - Essex
See all 4,682 properties in Shelter Island Heights
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 Wi-Fi, an outdoor pool and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms in ...
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 Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
9.6/10 Exceptional! (56 reviews)
"Very new and clean property very helpful and friendly staff ..... some areas where the rvs are the view not great ..... otherwise all good"

Reviewed on 18 Sept 2026

North Fork Resort
The Surf Club

The Surf Club

3.5 out of 5
20 Surfside Avenue Montauk NY
Stay at this beach aparthotel in Montauk. Enjoy free Wi-Fi, a beach locale and room service. Popular attractions Montauk Point Lighthouse and Montauk Point are ...
The Surf Club
See all properties in Shelter Island Heights
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 care-free afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
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Cities near Shelter Island Heights

A calm lake with a forest in the background during sunset.

Southold

A lighthouse on a rocky outcrop with a boat in the water.

Orient

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