Name: Pier Blue Inn Old Saybrook - Essex
Price range: P4,658
Rating: 7.8

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

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.

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 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 Sep 11, 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 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 Aug 23, 2025

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Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd, Old Saybrook, CT

P4,658

P5,357 total

Sep 29 - Sep 30

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! (1,011 reviews)

"Highly recommend!"

Reviewed on Sep 21, 2025

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

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 Sep 19, 2025

Windward Shores Ocean Resort

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 Sep 2, 2025

Montauk Oceanside Suites

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 Sep 16, 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.

Check Shelter Island Heights hotel availability

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.

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.

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.

Things to do

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

P8,435

per adult

From Mattituck: North Fork Area Bike Tour with Food Tasting

P7,922