Shelter Island Heights, NY

Travel Guide

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

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

4.5/5(10 area reviews)

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

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.

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! (79 reviews)
"The Pridwin is a beautiful property with a stunning view and old New England, Americana historic vibe. It is a quintessential experience if you want to have quiet yet convenience to both the north and south forks. The ferry is quick and the island is beautiful and quiet if you go during off season. ..."

Reviewed on 2025/9/28

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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! (36 reviews)
"Always a sold stay on Shelter Island"

Reviewed on 2025/8/23

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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 NT$2,433 per night from Oct 7 to Oct 8
NT$2,433
NT$2,798 total
Oct 7 - Oct 8
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. ...
7.8/10 Good! (1,004 reviews)
"For a budget hotel its not bad - area is generally pricy - its just needs a facelift - it needs to remove the carpets. Staff is nice."

Reviewed on 2025/10/4

Pier Blue Inn Old Saybrook - Essex
See all 4,736 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.
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! (296 reviews)
"The non ocean view rooms are fabulous. I’m sure the ocean side ones are great."

Reviewed on 2025/9/30

Windward Shores Ocean Resort
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! (1,251 reviews)
"Beautiful grounds, excellent staff"

Reviewed on 2025/9/30

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! (414 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 2025/9/16

Montauk Oceanside Suites
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.

Sunset Beach

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.

Crescent Beach

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.

Shelter Island Country Club