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 care-free afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
Crescent Beach
Why not spend a care-free afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
Things to do
Private Vacation Photoshoot with Photographer in The Hamptons
RM1,123
per adult
Top hotels in The Heights
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is RM1,011 per night from 20 Apr to 21 Apr
RM1,011
RM1,232 total
20 Apr - 21 Apr
includes taxes & fees
Stay at this beach resort in Westbrook. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.8/10 Excellent! (1,001 reviews)
Enjoyable stay.
Reviewed on 28 Mar 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is RM683 per night from 3 May to 4 May
RM683
RM1,127 total
3 May - 4 May
includes taxes & fees
Stay at this beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.4/10 Very Good! (627 reviews)
Really enjoyed our stay at the soundview. You are able to easily hear neighbors so just an FYI. Love being so close to the water and hearing the water and waves at night. Overnight oats at breakfast were my favorite.
Reviewed on 2 Apr 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is RM562 per night from 5 Apr to 6 Apr
RM562
RM646 total
5 Apr - 6 Apr
includes taxes & fees
Stay at this business-friendly hotel in Southampton. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (456 reviews)
Spacious suite. Wish our stay was longer. Very clean, lots of special touches. Great staff.
Reviewed on 2 Apr 2026
The Harbor Front Inn
209 Front St Greenport NY
The price is RM701 per night from 29 Apr to 30 Apr
RM701
RM916 total
29 Apr - 30 Apr
includes taxes & fees
Stay at this business-friendly hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is RM287 per night from 9 Apr to 10 Apr
RM287
RM330 total
9 Apr - 10 Apr
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8/10 Very Good! (1,001 reviews)
Parking was easy and secure. Heat worked perfectly.
Reviewed on 3 Apr 2026
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is RM757 per night from 22 Apr to 23 Apr
RM757
RM966 total
22 Apr - 23 Apr
includes taxes & fees
Stay at this hotel in Southold. Enjoy free Wi-Fi, free bicycles on-site and a business centre. Our guests praise the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (253 reviews)
Simply delightful!
Reviewed on 30 Mar 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.
