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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is £69 per night from 18 May to 19 May
£69
18 May - 19 May
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)
If you can look beyond the immediate exterior and sense of disrepair (it's not...), then you can enjoy the stay here. While there is no swimming pool, the property is well positioned to the coast and local beaches. They were doing some road construction immediately outside the property and on the ...
Reviewed on 15 May 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is £145 per night from 21 May to 22 May
£145
21 May - 22 May
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! (497 reviews)
Great for dogs - huge fenced yard
Reviewed on 11 May 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is £315 per night from 28 May to 29 May
£315
28 May - 29 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! (647 reviews)
They charged us for parking in front of our room. Unbelievable. We stayed there in April, off season, the motel was empty.
Reviewed on 11 May 2026
Sag Harbor Inn
45 West Water Street Sag Harbor NY
The price is £330 per night from 7 Jun to 8 Jun
£330
7 Jun - 8 Jun
includes taxes & fees
Stay at this business-friendly hotel in Sag Harbor. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (613 reviews)
Nice room and view
Reviewed on 15 May 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is £228 per night from 25 May to 26 May
£228
25 May - 26 May
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! (1,005 reviews)
Very nice place. Great location.
Reviewed on 15 May 2026
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is £206 per night from 25 May to 26 May
£206
25 May - 26 May
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! (269 reviews)
Very helpful staff. Room was very roomy (no pun intented) and appeared to be recently upgraded. Chit provided for continental breakfast at a local coffee shop that was very good. Definitely recommend.
Reviewed on 5 May 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.
