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
P17,127
per adult
Top hotels in The Heights
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is P8,715 per night from Mar 11 to Mar 12
P8,715
P11,630 total
Mar 11 - Mar 12
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! (610 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...
Reviewed on Jan 10, 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
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! (1,002 reviews)
Room was clean and warm and the staff was very friendly
Reviewed on Feb 1, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is P11,449 per night from Feb 16 to Feb 17
P11,449
P14,177 total
Feb 16 - Feb 17
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)
Great room and staff
Reviewed on Jan 14, 2026
Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
The price is P5,926 per night from Feb 16 to Feb 17
P5,926
P6,815 total
Feb 16 - Feb 17
includes taxes & fees
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,000 reviews)
Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area.
Reviewed on Jan 28, 2026
The Harbor Front Inn
209 Front St Greenport NY
The price is P8,197 per night from Feb 22 to Feb 23
P8,197
P11,039 total
Feb 22 - Feb 23
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! (566 reviews)
Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return!
Reviewed on Feb 6, 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is P7,389 per night from Feb 16 to Feb 17
P7,389
P8,501 total
Feb 16 - Feb 17
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 ...
9.4/10 Exceptional! (434 reviews)
Adorable room
Reviewed on Jan 28, 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.
