Shelter Island Heights

Travel 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 €440 per night from 24 Feb to 25 Feb
€440
per night
24 Feb - 25 Feb
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 ...
8.2/10 Very Good! (729 reviews)
The room Was ready early and spotless The stuffy lobsters for the girls was a nice touch

Reviewed on 16 Feb 2026

Gurney's Montauk Resort & Seawater Spa
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is €168 per night from 25 Mar to 26 Mar
€168
per night
25 Mar - 26 Mar
Stay at this beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.4/10 Very Good! (614 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on 10 Jan 2026

Sound View Greenport
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is €194 per night from 28 Feb to 1 Mar
€194
per night
28 Feb - 1 Mar
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 ...
9/10 Wonderful! (1,297 reviews)
Room was very nice

Reviewed on 17 Feb 2026

Montauk Manor
See all 4,744 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 ...
9/10 Wonderful! (1,297 reviews)
Room was very nice

Reviewed on 17 Feb 2026

Montauk Manor
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

Westbrook CT
Stay at this beach cottage in Westbrook. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Westbrook Town Beach and Clinton Plaza ...
9.6/10 Exceptional! (75 reviews)
Great location and service.

Reviewed on 11 Sept 2025

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Hampton Bays NY
Stay at this beach holiday home in Hampton Bays. Enjoy a beach locale, a garden and laundry facilities. Popular attractions Meschutt Beach and Good Ground Park ...
9.4/10 Exceptional! (131 reviews)
We absolutely loved the place and had a great time. There was plenty of space for the kids to spread out and enjoyed the indoor fireplace. The sunrise views were amazing and it's always special to stay on the water. Communication with the owner was great. We hope to visit again.

Reviewed on 11 Jan 2026

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
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
Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA

Southold

beach of east marion seen from water side

East Marion

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