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! (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 27 Jul 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 ...
8.8/10 Excellent! (32 reviews)
"we loved it!"

Reviewed on 9 Jul 2025

The Chequit
Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is €483 per night from 2 Sept to 3 Sept
€483
2 Sept - 3 Sept
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! (206 reviews)
"Great location with a relaxed vibe, but not without flaws The location is unbeatable, and the low-key atmosphere is a real plus. That said, it’s definitely pricey for what you get—you’re mostly paying for the beachfront setting. The beach is beautiful, and the counter-service restaurant is fantastic ..."

Reviewed on 6 Aug 2025

Marram
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! (1,226 reviews)
"Beautiful full service facility. We stayed in a friends unit which was lovely. The only complaint would be that when the pool is busy on summer weekends and the restaurant isn’t, it would be lovely if the waitresses could let patrons order drinks. It only happened once on the 3 night stay all of ..."

Reviewed on 4 Aug 2025

Montauk Manor
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 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 8 Aug 2025

Montauk Oceanside Suites
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 and South Edison Beach ...
8.4/10 Very Good! (268 reviews)
"Beach chairs and umbrella set up on the beach. No rush to set up your own. Clean, friendly accessible to all merchants and resturants"

Reviewed on 31 Jul 2025

The Surf Club
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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