Shelter Island Heights Travel Guide

Tourist Guide

coastal landscape at Greenport at the islands of shelter islands heights, county New York
coastal landscape at Greenport at the islands of shelter islands heights, county New York
View of Dering Harbor
View from the back patio of The Dory Restaurant on Shelter Island, NY #shelterisland #reflections #silence #nature
One of my favorite places, anywhere.  Reminiscent of the south of France, this little slice of heaven delivers every time.  Really cool French riverria vibe, with food and vin rose to boot.  Burratta on avocado puree with truffle oil, and fried artichoke hearts, with rose on ice (pictured) were only the beginning of yet another great al fresco meal, and memorable evening on Shelter Island.  We came by boat, anchored out, and swam in, but drive from the mainland, via the cute little 10 car ferry (part of the charm of making the trip).  Love, love this spot.

Where to stay in Shelter Island Heights

View from the back patio of The Dory Restaurant on Shelter Island, NY #shelterisland #reflections #silence #nature

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
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 ฿11,875 per night from 16 Mar to 17 Mar
฿11,875
฿16,280 total
16 Mar - 17 Mar
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! (735 reviews)
Staff wasn’t friendly, amenities not working, pools were closed, heating system in the room was very loud, made it hard to sleep.

Reviewed on 27 Feb 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is ฿4,694 per night from 30 Mar to 31 Mar
฿4,694
฿5,971 total
30 Mar - 31 Mar
includes taxes & fees
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! (1,299 reviews)
Always such a pleasure at the Manor.

Reviewed on 28 Feb 2026

Montauk Manor
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
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! (1,001 reviews)
Not fancy but very cute. Clean. Super nice staff. Cozy, delicious Indian restaurant right next door.

Reviewed on 1 Mar 2026

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 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! (1,299 reviews)
Always such a pleasure at the Manor.

Reviewed on 28 Feb 2026

Montauk Manor
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.

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