Name: Pier Blue Inn Old Saybrook - Essex
Price range: $106 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

$590 nightly

$675 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 ...

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

$92 nightly

$106 total

Aug 31 - Sep 1

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! (1,007 reviews)

"The vibe of PBG didn’t quite match up with my original expectations for a coastal beachside inn, but we had a great time. This was largely due to a room upgrade upon arrival and the kindness of the inn keeper. I’d request a room at the back of the property, which has a gorgeous view out onto the ..."

Reviewed on Aug 16, 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.

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' ...

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 ...

9.2/10 Wonderful! (1,387 reviews)

"It’s an olde roroperty overpriced for an early 2000’s condo style place."

Reviewed on Aug 15, 2026

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! (283 reviews)

"Property beautiful!Check out early"

Reviewed on Aug 14, 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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