Name: The Chequit
Rating: 8.8

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

When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.

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 Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...

9.4/10 Exceptional! (82 reviews)

Nice property

Reviewed on 13 Oct 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 Wi-Fi, free parking and premium bedding. Popular attractions Shelter Island Country Club and ...

8.8/10 Excellent! (37 reviews)

A cozy room with great pillows and quiet. Perfect little place.

Reviewed on 10 Oct 2025

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Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway, Montauk, NY

₹26,602

₹36,308 total

20 Nov - 21 Nov

includes taxes & fees

Stay at this 4-star beach resort in Montauk. Enjoy an outdoor pool, a full-service spa and 2 restaurants. Our guests praise the room service in their reviews. ...

8.2/10 Very Good! (675 reviews)

We had a lovely one night stay. Everyone was very friendly. Having my dogs there was a treat. The spa was great and relaxing. GIGI’s restaurant is a must. The only complaint I have is that the bedclothes need to be updated. They were torn/frayed in multiple places. Other than that it was a great ...

Reviewed on 11 Oct 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 Wi-Fi, an outdoor pool and a 24-hour fitness centre. Our guests praise the helpful staff and the clean ...

9/10 Wonderful! (1,257 reviews)

The women who checked us in were very sweet and kind. It made my wife think twice about getting too loud while in the throws of passion. She didn't want to cause them any headaches from complaints from other guests.

Reviewed on 20 Oct 2025

Montauk Oceanside Suites

115 South Emerson Avenue, Montauk, NY

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

8.4/10 Very Good! (415 reviews)

Property was clean and nice but did not smell good inside, it need candles and air freshener, also think something was off about the sewage system

Reviewed on 16 Sept 2025

Cliffside Resort Condominiums

61475 Route 48 (North Road), Greenport, NY

Stay at this 3-star beach aparthotel in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...

8.8/10 Excellent! (244 reviews)

Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in.

Reviewed on 11 Oct 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.

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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.

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.