Shelter Island Heights

Travel Guide

Photo by Erisa Dilo
Photo by tom owens
Photo by tom owens
Photo by Brian V. Rowe

Where to stay in Shelter Island Heights

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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

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.

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! (59 reviews)
"WELL APPOINTED"

Reviewed on 18 May, 2025

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 10 Nov, 2024

The Chequit
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
The price is S$128 per night from 29 Jun to 30 Jun
S$128
29 Jun - 30 Jun
includes taxes & fees
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. ...
7.6/10 Good! (972 reviews)
"Our check in was friendly and quick. VJ was pleasant and interested. There are many dining options nearby. Lovely, family owned and operated."

Reviewed on 9 Jun, 2025

Pier Blue Inn Old Saybrook - Essex
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! (1,193 reviews)
"I try to stay at the Montauk Manor once a year! It’s wonderful!!"

Reviewed on 11 Jun, 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! (284 reviews)
"Mother’s Day weekend for a family of 4. From start to finish, the stay was amazing. The check-in was so simple. The room was exactly how the photos showed. It was clean and roomy. The beach is a very short walk away. Even though the pool was not officially open yet, it looked wonderful. We have already ..."

Reviewed on 12 May, 2025

Windward Shores Ocean Resort
Montauk Oceanside Suites
Montauk Oceanside Suites
3 out of 5
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! (380 reviews)
"Close by to everything. Neighbors can be noisy, but that doesn't reflect on the property."

Reviewed on 27 May, 2025

Montauk Oceanside Suites
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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Things to do