Name: Pier Blue Inn Old Saybrook - Essex
Price range: $100 total
Rating: 8

Where to stay in Shelter Island Heights

Find the best Shelter Island Heights areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island Heights

A calm lake reflecting trees and a clear sky.

The Heights

If you're spending some time in The Heights, Sunset Beach and Shelter Island Country Club are top sights worth seeing.

A calm lake with reflections of clouds, surrounded by trees and a distant structure.

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

$610 nightly

$697 total

Sep 13 - Sep 14

Total with taxes and fees

Book a stay at this beach hotel in Shelter Island Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

The Chequit

23 Grand Ave Shelter Island Heights NY

$293 nightly

$334 total

Sep 8 - Sep 9

Total with taxes and fees

Stay at this hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Shelter Island Country Club and Sunset ...

9.2/10 Wonderful! (52 reviews)

"Room small but very functional, well decorated, bath modern, and very upscale. First night the attendant was wonderful. That was on the 18th. Next day, we had a leak at the shower because the molding on shower door was not working correctly, and the floor got wet. Staff was not really very responsive ..."

Reviewed on Aug 20, 2026

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Fully refundableReserve now, pay when you stay

$87 nightly

$100 total

Aug 23 - Aug 24

Total with taxes and 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. ...

8/10 Very Good! (1,011 reviews)

"Clean and comfortable room. Very dated furniture."

Reviewed on Aug 19, 2026

See all 4,741 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.

North Fork Resort

690 Queen St Greenport NY

Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...

9.6/10 Exceptional! (50 reviews)

"THERE WAS ONLY ONE THING. THE LAST MORNING THERE WAS NO HOT H2O HOWEVER THE PROBLEM WAS FIXED."

Reviewed on Aug 20, 2026

Montauk Manor

236 Edgemere St. Montauk NY

Stay at this aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...

Cliffside Resort Condominiums

61475 Route 48 (North Road) Greenport NY

Book a stay at this beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...

9/10 Wonderful! (285 reviews)

"great property! but couple of downsides- check in time is 5:00 pm, although they make it possible to get to room way earlier (3:00 pm). But check out time is 10:00 am which is really early and oractically does not give you enough time to do anything that day. For this type of a resort I wold expect ..."

Reviewed on Aug 18, 2026

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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.

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Stay near popular Shelter Island Heights attractions

Sunset Beach

9.4/10 (14 reviews)

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.

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