Shelter Island Heights, NY

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

4.5/5(10 area reviews)

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 AED 1,230 per night from Feb 10 to Feb 11
AED 1,230
AED 1,686 total
10 Feb - 11 Feb
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! (719 reviews)
Staying at Gurney's after their many renovations was surprising !! The rooms don't look outdated anymore including the Spa / Pool area - for the price you're paying per night, I appreciated the face lift. Oceanviews from any angle of this hotel site will always be incredible !

Reviewed on 12 January 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
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. ...
7.8/10 Good! (1,002 reviews)
I have stayed here a number of times, and each time the room has been spotless and smells fresh. The staff is very friendly and always offers to help in some way, whether it's to get the snow off my car or provide bottled water. I will be staying here again!

Reviewed on 23 January 2026

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Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is AED 493 per night from Feb 2 to Feb 3
AED 493
AED 668 total
2 Feb - 3 Feb
includes taxes & fees
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (608 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 January 2026

Sound View Greenport
See all 4,719 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 WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,287 reviews)
Everyone was perfect for our stay at the Montauk Manor!!! The lobby is beautiful and clean. The staff was friendly and very welcoming. We enjoyed massages with Amy, which I highly recommend. Breakfast was delicious at Monte’s (restaurant in the lobby). We loved our room it was immaculate and had ...

Reviewed on 26 January 2026

Montauk Manor
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Southampton NY
Book a stay at this family-friendly vacation home in Southampton. Enjoy free WiFi, private pools, and a garden. Popular attractions Southampton Golf Range and ...
9.8/10 Exceptional! (32 reviews)
The perfect spot for our niece’s wedding weekend.The property is spacious and well appointed. Close to everything but still feels private. Comfortable beds and sitting areas. The pool was amazing and a great spot to relax between wedding events. We had 7 adults stay there was plenty of room for everyone. ...

Reviewed on 26 September 2025

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

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

Hampton Bays NY
Book a stay at this beach vacation home in Hampton Bays. Enjoy a beach locale, a garden, and laundry facilities. Popular attractions Meschutt Beach and Good ...
9.4/10 Exceptional! (129 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 January 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 carefree afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.

Sunset Beach

Crescent Beach

Why not spend a carefree afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.

Crescent Beach

Menhadden Lane Beach

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

Menhadden Lane Beach