Shelter Island Heights Travel Guide

Tourist 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

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The Heights

4/5(1 area review)

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! (77 reviews)
"Shelter Island is definitely a gem"

Reviewed on 11 Sept 2025

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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 23 Aug 2025

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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 NZ$160 per night from 29 Sept to 30 Sept
NZ$160
29 Sept - 30 Sept
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! (1,010 reviews)
"Highly recommend!"

Reviewed on 21 Sept 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,753 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

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! (1,250 reviews)
"Great"

Reviewed on 19 Sept 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! (295 reviews)
"Very nice & affordable"

Reviewed on 2 Sept 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 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 16 Sept 2025

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 care-free afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.

Sunset Beach

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.

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

Activities

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

NZ$253
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

NZ$237
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Shelter Island Heights

Cities near Shelter Island Heights

Photo by tom owens

Shelter Island