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
฿5,747
per adult
Half Day(PM) North Fork Private Wine & Food Tour by Local Expert
฿10,824
per adult
Top hotels in The Heights
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿8,860 per night from 12 May to 13 May
฿8,860
฿12,892 total
12 May - 13 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 ...
8.6/10 Excellent! (645 reviews)
Beautiful place to stay on a special getaway
Reviewed on 7 May 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is ฿4,810 per night from 10 May to 11 May
฿4,810
฿5,528 total
10 May - 11 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! (486 reviews)
The staff were great and the rooms were in greay shape and very comfortable. The location is close to many restaurants.
Reviewed on 7 May 2026
Sag Harbor Inn
45 West Water Street Sag Harbor NY
The price is ฿8,889 per night from 14 May to 15 May
฿8,889
฿10,155 total
14 May - 15 May
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! (609 reviews)
Beautiful hotel facing the harbor with courteous service and staff.
Reviewed on 8 May 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is ฿2,637 per night from 17 May to 18 May
฿2,637
฿3,033 total
17 May - 18 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! (1,005 reviews)
Very clean bare-bones hotel in a quiet location. Large rooms. Nice breakfast place across the road and a short drive to more services and stores. Helpful staff. Only criticism -- and it's an important one -- is that there were no friction strips or other kind of safety on the bathtub, so it was unexpectedly ...
Reviewed on 7 May 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ฿7,243 per night from 20 May to 21 May
฿7,243
฿8,887 total
20 May - 21 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! (1,002 reviews)
Great views from the restaurant and bar area. Staff were very friendly and attentive. Will stay here again.
Reviewed on 8 May 2026
Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
The price is ฿3,819 per night from 2 Jun to 3 Jun
฿3,819
฿4,392 total
2 Jun - 3 Jun
includes taxes & fees
Stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7.8/10 Good! (1,007 reviews)
Clean and quality hotel ***. Friendly and helpful staff.
Reviewed on 7 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.
