Where to stay in Shelter Island Heights

The Heights

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

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.

The Pridwin Hotel

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! (69 reviews)

"Beautifully designed property with several unique and inviting spaces. Very comfortable room and bed and we took advantage of the complimentary use of the kayaks and paddle boards and easy access to the beach. The staff at the front desk and the pool bar were extremely friendly and laid back. Lovely ..."

Reviewed on Jul 27, 2025

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The Chequit

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 ...

8.8/10 Excellent! (32 reviews)

"we loved it!"

Reviewed on Jul 9, 2025

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Marram

21 Oceanview Terrace, Montauk, NY

P18,697

P32,120 total

Sep 2 - Sep 3

includes taxes & fees

Stay at this 4-star beach hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Montauk Point Lighthouse and Montauk Point ...

8.6/10 Excellent! (209 reviews)

"Great location! Highly recommend."

Reviewed on Aug 12, 2025

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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

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! (1,230 reviews)

"I had the best time and highly recommend this hotel!"

Reviewed on Aug 10, 2025

Montauk Oceanside Suites

115 South Emerson Avenue, Montauk, NY

Stay at this 3-star aparthotel in Montauk. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Montauk Point and South Edison Beach are located ...

8.4/10 Very Good! (402 reviews)

What you see is what you get

"Room was exactly as shown in the pictures. Worked well for our family of four. The pull-out couch bed could be better but we didn't have high expectations for that. Overall unit was spacious and suited us well for the trip. Loved being close to the stores and right across from the beach. Good ..."

Reviewed on Aug 8, 2025

The Surf Club

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 and South Edison Beach ...

8.6/10 Excellent! (270 reviews)

"The front desk was great !!"

Reviewed on Aug 10, 2025

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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.

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.

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.

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

P8,608

per adult

From Mattituck: North Fork Area Bike Tour with Food Tasting

P8,085