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.
Top hotels in The Heights
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is £215 per night from 5 Apr to 6 Apr
£215
5 Apr - 6 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! (1,000 reviews)
The room was perfect, staff was excellent, parking was right next to my room. Best Breakfast Sausage ever.
Reviewed on 24 Mar 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is £173 per night from 19 Apr to 20 Apr
£173
19 Apr - 20 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 ...
8.4/10 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 23 Mar 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is £121 per night from 26 Apr to 27 Apr
£121
26 Apr - 27 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! (452 reviews)
Very nice
Reviewed on 27 Mar 2026
The Harbor Front Inn
209 Front St Greenport NY
The price is £149 per night from 15 Apr to 16 Apr
£149
15 Apr - 16 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 ...
8.8/10 Excellent! (577 reviews)
Perfect
Reviewed on 26 Mar 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is £62 per night from 29 Mar to 30 Mar
£62
29 Mar - 30 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! (1,004 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 28 Mar 2026
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is £152 per night from 8 Apr to 9 Apr
£152
8 Apr - 9 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! (250 reviews)
Clean, spacious and thoughtful room amenities. Close by to town and great restaurants.
Reviewed on 23 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.
