Shelter Island Heights

Travel Guide

Photo by Erisa Dilo
Photo by Erisa Dilo
Photo by tom owens
Photo by tom owens
Photo by tom owens
Photo by tom owens
Photo by Brian V. Rowe
Photo by Brian V. Rowe

Where to stay in Shelter Island Heights

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The Heights

If you're spending some time in The Heights, Sunset Beach and Shelter Island Country Club are top sights worth seeing.

The Heights
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Hay Beach

When in Hay Beach, you can plan a visit to Greenport Carousel and Railroad Museum of Long Island, some noteworthy sights in the nearby area.

Hay Beach
Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
The price is €161 per night from 26 Feb to 27 Feb
€161
includes taxes & fees
26 Feb - 27 Feb
Stay at this 3.5-star aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,124 reviews)
"JUst a fun annual trip to relax for a couple of days. Always fun"

Reviewed on 24 Feb 2025

Montauk Manor
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
The price is €203 per night from 11 Mar to 12 Mar
€203
includes taxes & fees
11 Mar - 12 Mar
Stay at this 3.5-star beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
8.6/10 Excellent! (1,003 reviews)
"Love staying here! We are from Ohio, but stay here when we come out to east coast. Beautiful Historic Hotel."

Reviewed on 21 Feb 2025

Water's Edge Resort & 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 €76 per night from 2 Mar to 3 Mar
€76
includes taxes & fees
2 Mar - 3 Mar
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. ...
7.6/10 Good! (920 reviews)
"Perfect place for our short stay, super clean and comfortable!"

Reviewed on 17 Feb 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,703 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 3.5-star aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,124 reviews)
"JUst a fun annual trip to relax for a couple of days. Always fun"

Reviewed on 24 Feb 2025

Montauk Manor
Montauk Oceanside Suites
Montauk Oceanside Suites
3 out of 5
115 South Emerson Avenue, Montauk, NY
Stay at this 3-star aparthotel in Montauk. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Montauk Point and South Edison Beach are ...
8.4/10 Very good! (362 reviews)
"I didn’t realize the property was mobile check-in and that all communication would be automated in the winter season. if you guys had that more clear on the Expedia it would be awesome. Otherwise the stay was great, clean room, no hassle to get in, right by the beach."

Reviewed on 17 Feb 2025

Montauk Oceanside Suites
Windward Shores Ocean Resort
Windward Shores Ocean Resort
3 out of 5
2062 Montauk Highway, PO Box 7031, Amagansett, NY
Stay at this 3-star beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (274 reviews)
"Everything Was Great The Only Issues Were The Fridge Was Not Getting Cold And The Bed Was Not Comfortable But Property was Great"

Reviewed on 21 Feb 2025

Windward Shores Ocean Resort
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.

Popular places to visit

Sunset Beach

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.

Sunset Beach

Crescent Beach

Why not spend a care-free afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.

Crescent Beach

Menhadden Lane Beach

Why not spend a care-free afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?

Menhadden Lane Beach
Southold

Southold

Photo by Benny Goh

East Marion