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

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
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Hay Beach

Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

Hay Beach
The Pridwin Hotel
The Pridwin Hotel
4 out of 5
81 Shore Road, Shelter Island Heights, NY
Stay at this 4-star beach hotel in Shelter Island Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (63 reviews)
"Lovely hotel/ resort. Look forward to going again!"

Reviewed on Jun 24, 2025

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The Pridwin Hotel
The Chequit
The Chequit
3 out of 5
23 Grand Ave, Shelter Island Heights, NY
Stay at this 3-star hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Shelter Island Country Club and ...
8.6/10 Excellent! (29 reviews)
"Excellent"

Reviewed on Nov 10, 2024

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The Chequit
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is P6,216 per night from Jul 13 to Jul 14
P6,216
P7,149 total
Jul 13 - Jul 14
includes taxes & fees
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,001 reviews)
"Great location and pool, close to a wonderful restaurant"

Reviewed on Jun 30, 2025

Quality Inn Old Saybrook - Westbrook
See all 4,836 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! (1,204 reviews)
"Nice"

Reviewed on Jul 2, 2025

Montauk Manor
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! (286 reviews)
Decent and Better priced
"A good choice for “affordable” stays in the Hamptons. The place is not “fresh” or chic by any means but it’s very acceptable and half the price of many other accommodations. Over all it’s a good value. Clean, well located and homey."

Reviewed on Jun 28, 2025

Windward Shores Ocean Resort
The Surf Club
The Surf Club
3.5 out of 5
20 Surfside Avenue, Montauk, NY
Stay at this 3.5-star beach aparthotel in Montauk. Enjoy free WiFi, a beach locale, and room service. Popular attractions Montauk Point Lighthouse and Montauk ...
8.4/10 Very Good! (260 reviews)
"The hotel property and beach were very nicer the accommodations were tight for 4 adults. My twins are 18. The sofa bed was old and very uncomfortable. For the price you pay they should have comfortable accommodations for the sofa bed guests."

Reviewed on Jun 27, 2025

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.

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

Shelter Island Country Club

Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.

Shelter Island Country Club

Things to do

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

P8,933
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Vetted Flights and food pairings at local winery.

Long Island North Fork Sights Bites & Flights, Half-Day Tour: AM

P19,045
per adult
Long Island North Fork Sights Bites & Flights, Half-Day Tour: AM
See all activities in Shelter Island Heights
Photo by tom owens

Shelter Island