The Heights
Shelter Island Heights
Visit The Heights
Popular places to visit
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.
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.
Things to do
Private Vacation Photoshoot with Photographer in The Hamptons
P16,668
per adult
Top hotels in The Heights
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is P13,379 per night from Apr 1 to Apr 2
P13,379
P16,430 total
Apr 1 - Apr 2
includes taxes & fees
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,000 reviews)
The room was perfect, staff was excellent, parking was right next to my room. Best Breakfast Sausage ever.
Reviewed on Mar 24, 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is P10,758 per night from Apr 27 to Apr 28
P10,758
P14,020 total
Apr 27 - Apr 28
includes taxes & fees
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (625 reviews)
Lovely hotel. Amazing location. Gorgeous views. Breakfast was good continental. It rained hard and we had some water leaking in the door from the back deck. Mentioned it to the front desk when we checked out. Could’ve posed a Could’ve posed a slipping hazard.Otherwise, I would’ve given five ...
Reviewed on Mar 23, 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is P8,556 per night from Apr 8 to Apr 9
P8,556
P9,836 total
Apr 8 - Apr 9
includes taxes & fees
Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (452 reviews)
Very nice
Reviewed on Mar 27, 2026
The Harbor Front Inn
209 Front St Greenport NY
The price is P8,965 per night from Apr 15 to Apr 16
P8,965
P11,972 total
Apr 15 - Apr 16
includes taxes & fees
Book a stay at this business-friendly hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (577 reviews)
Perfect
Reviewed on Mar 26, 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
The price is P4,228 per night from Mar 29 to Mar 30
P4,228
P4,862 total
Mar 29 - Mar 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. ...
8/10 Very Good! (1,004 reviews)
It was clean, easy to find, safe and convenient to park, and a pleasant stay for an overnight in the area for a family event. We’d absolutely return.
Reviewed on Mar 28, 2026
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is P10,201 per night from Apr 15 to Apr 16
P10,201
P13,161 total
Apr 15 - Apr 16
includes taxes & fees
Stay at this hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (250 reviews)
Clean, spacious and thoughtful room amenities. Close by to town and great restaurants.
Reviewed on Mar 23, 2026
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.
