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 £205 per night from 6 Apr to 7 Apr
£205
6 Apr - 7 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 £174 per night from 19 Apr to 20 Apr
£174
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 £123 per night from 29 Apr to 30 Apr
£123
29 Apr - 30 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! (455 reviews)
Loved the place, clean and helpfull staff.
Reviewed on 30 Mar 2026
The Harbor Front Inn
209 Front St Greenport NY
Fully refundable
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 ...
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is £62 per night from 6 Apr to 7 Apr
£62
6 Apr - 7 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! (1,006 reviews)
Room could have been cleaner. The floor was dirty. The room also looked worn and in need of updating. The tub faucet dripped constantly, but the shower was nice. Staff was friendly. I was surprised they don’t offer daily housekeeping. Bed was comfortable. It was great that the room had a microwave ...
Reviewed on 30 Mar 2026
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is £163 per night from 16 Apr to 17 Apr
£163
16 Apr - 17 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! (252 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.
