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.
Top hotels in The Heights
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is HK$1,050 per night from 2 Apr to 3 Apr
HK$1,050
HK$1,343 total
2 Apr - 3 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! (1,002 reviews)
We loved our stay here. The staff was so wonderful! (Mary Luz at the Starbucks was so sweet!) and the food was fresh and delicious. The waitstaff was attentive and cognizant and caring regarding food allergies. The views from every vantage were special and memorable. We had not great weather and ...
Reviewed on 18 Mar 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is HK$1,346 per night from 5 Apr to 6 Apr
HK$1,346
HK$1,762 total
5 Apr - 6 Apr
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 ...
8.6/10 Excellent! (621 reviews)
Staff was over the top helpful, nice!!!! If you needed help or anything they were right on it for you Thank you do very much for making a sad trip for a loved ones memorial into something grateful!!
Reviewed on 1 Mar 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is HK$1,026 per night from 5 Apr to 6 Apr
HK$1,026
HK$1,180 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! (449 reviews)
By far one of the best hotels I’ve ever stayed at. The bed was heaven, the room was huge and decorated so well!
Reviewed on 18 Mar 2026
The Harbor Front Inn
209 Front St Greenport NY
The price is HK$1,051 per night from 22 Mar to 23 Mar
HK$1,051
HK$1,425 total
22 Mar - 23 Mar
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 ...
8.8/10 Excellent! (574 reviews)
Everything was great! Loved the continental breakfast.
Reviewed on 15 Mar 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is HK$627 per night from 22 Mar to 23 Mar
HK$627
HK$721 total
22 Mar - 23 Mar
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! (1,000 reviews)
Very welcoming staff. Average accommodations but comfortable and convenient to supermarket.
Reviewed on 9 Mar 2026
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is HK$1,127 per night from 25 Mar to 26 Mar
HK$1,127
HK$1,288 total
25 Mar - 26 Mar
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! (245 reviews)
Fine
Reviewed on 15 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.
