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.

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

CA $640

CA $804 total

Aug 5 - Aug 6

includes taxes & fees

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! (65 reviews)

Beautiful hotel

"Beautiful place"

Reviewed on Jul. 13, 2025

The Chequit

23 Grand Ave, Shelter Island Heights, NY

CA $744

CA $850 total

Jul 15 - Jul 16

includes taxes & fees

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! (30 reviews)

"we loved it!"

Reviewed on Jul. 9, 2025

Marram

21 Oceanview Terrace, Montauk, NY

CA $646

CA $996 total

Jul 16 - Jul 17

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! (180 reviews)

"We loved our stay at Marram! The property is a little slice of beach magic. The location was absolutely perfect, and the private beach was exactly what we were hoping for. Tranquil and beautiful, they have effortlessly blended luxury into the unpretentious surf town vibes that Montauk is known for. ..."

Reviewed on Jul. 10, 2025

See all 4,863 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

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! (1,210 reviews)

"Beautiful property and spacious rooms"

Reviewed on Jul. 7, 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 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

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 Lighthouse and Montauk Point ...

8.4/10 Very Good! (389 reviews)

"good location, short walk to beach. modern room.. walk to town 3 short blocks"

Reviewed on Jun. 30, 2025

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.

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.