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
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is £133 per night from 17 May to 18 May
£133
17 May - 18 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! (496 reviews)
Great for dogs - huge fenced yard
Reviewed on 11 May 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is £334 per night from 31 May to 1 Jun
£334
31 May - 1 Jun
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 £266 per night from 2 Jun to 3 Jun
£266
2 Jun - 3 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! (612 reviews)
I’ve stayed there probably 10 times. They never remember me. Never an upgrade or a perk. I continue to go back because it’s just a solid choice. Clean hotel, nice staff, predictable and quiet. If your a single traveler, retired couple, business traveler that just needs a place to sleep than this ...
Reviewed on 14 May 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is £65 per night from 21 May to 22 May
£65
21 May - 22 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! (1,002 reviews)
Excellent location. Parking great and surrounding area abounds with things to do while visiting.
Reviewed on 13 May 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is £203 per night from 21 May to 22 May
£203
21 May - 22 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! (1,004 reviews)
We had a nice stay. Enjoyed having a drink at the bar and listening to the band. Had a nice breakfast in the morning. No major complaints, but for the price and style of the hotel I expected it to be cleaner. One of my drinks in the bar had a dirty ice cube and the glassware and plates at breakfast ...
Reviewed on 14 May 2026
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is £202 per night from 28 May to 29 May
£202
28 May - 29 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.
