Name: Pier Blue Inn Old Saybrook - Essex
Price range: $111 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

$683 nightly

$780 total

Jul 19 - Jul 20

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. ...

9.6/10 Exceptional! (91 reviews)

"We had such an amazing time at the Pridwin! The hotel is gorgeous and everything is kept clean and organized for guests!"

Reviewed on Jul 5, 2026

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$1,196 nightly

$1,366 total

Jul 26 - Jul 27

Total with taxes and fees

Book a stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Popular attractions Hither Woods Preserve and Hither ...

8.4/10 Very Good! (821 reviews)

"-"

Reviewed on Jul 10, 2026

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

$96 nightly

$111 total

Jul 13 - Jul 14

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! (1,015 reviews)

"Still the same wonderful little place as the last time I stayed here!"

Reviewed on Jul 11, 2026

See all 4,760 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 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! (1,365 reviews)

"Rooms and facilty were clean and room was reasonably spacious. Comfortable bed. Nice kitchenette and balcony. Breakfast in b the restaurant was good. Outdoor pool very nice and heated. Close to most areas of interest. Shuttle available but we did not use."

Reviewed on Jul 9, 2026

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' ...

9.4/10 Exceptional! (30 reviews)

"Overall the stay was pleasant. The cottages are well maintained. This property is still developing so there was active construction. It listed some amenities that were not yet available and some that were only available through a weekend stay which we did not have with a Sunday-Tuesday booking. I ..."

Reviewed on Jul 8, 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! (269 reviews)

"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"

Reviewed on Jul 11, 2026

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.

Check Shelter Island Heights hotel availability

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.

See properties