The Heights Travel Guide
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 Luxury Wine Tours of Long Island Pindar Winery
฿5,588
per adult
Long Island Wine Tour North Fork Sights Bites Flights Half Day PM
฿10,524
per adult
Top hotels in The Heights
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is ฿5,433 per night from 1 Apr to 2 Apr
฿5,433
฿6,799 total
1 Apr - 2 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! (1,004 reviews)
This was my first time at Water’s Edge and will definitely not be my last. Our stay was wonderful. Becky at the front desk was
Reviewed on 7 Mar 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿4,834 per night from 25 Mar to 26 Mar
฿4,834
฿6,426 total
25 Mar - 26 Mar
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! (620 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 ฿4,184 per night from 18 Mar to 19 Mar
฿4,184
฿4,812 total
18 Mar - 19 Mar
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! (446 reviews)
Clean room. The man at the office was very friendly.
Reviewed on 10 Mar 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
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 ฿5,351 per night from 16 Mar to 17 Mar
฿5,351
฿6,113 total
16 Mar - 17 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! (244 reviews)
Very friendly
Reviewed on 6 Mar 2026
The Harbor Front Inn
209 Front St Greenport NY
The price is ฿4,238 per night from 22 Mar to 23 Mar
฿4,238
฿5,745 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! (572 reviews)
Room was clean, climate control worked well kept room comfortable, bathroom was nice. Only thing I would suggest would be a complementary bottle of water for each guest.
Reviewed on 10 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.
