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 carefree afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
Crescent Beach
Why not spend a carefree afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
Things to do
Long Island Wine and Food Day Trip with Sommelier host from NYC
￥21,679
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
￥20,361
per adult
The Heights Hotel Deals
The Chequit
23 Grand Ave, Shelter Island Heights, NY
Stay at this 3-star hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Shelter Island Country Club and ...
8.8/10 Excellent! (36 reviews)
"Always a sold stay on Shelter Island"
Reviewed on Aug 23, 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
The price is ￥12,037 per night from Oct 8 to Oct 9
￥12,037
￥13,843 total
Oct 8 - Oct 9
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.8/10 Good! (1,004 reviews)
"For a budget hotel its not bad - area is generally pricy - its just needs a facelift - it needs to remove the carpets. Staff is nice."
Reviewed on Oct 4, 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
The price is ￥14,051 per night from Nov 2 to Nov 3
￥14,051
￥16,158 total
Nov 2 - Nov 3
includes taxes & fees
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,005 reviews)
"Overall, a nice hotel for a one day trip! :)"
Reviewed on Oct 5, 2025
Sound View Greenport
58775 County Rd 48, Greenport, NY
The price is ￥35,574 per night from Oct 21 to Oct 22
￥35,574
￥47,997 total
Oct 21 - Oct 22
includes taxes & fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (577 reviews)
"Nice views on sunset"
Reviewed on Oct 3, 2025
The Atlantic Hotel
1655 County Road 39, Southampton, NY
Book a stay at this business-friendly hotel in Southampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7/10 Good! (944 reviews)
"Really more of a motel not a hotel. Room was basic but adequate and clean. Close to Southampton. They were fully booked on one of the weekend days of our stay so rate that night was high for this type of lodging."
Reviewed on Sep 30, 2025
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
The price is ￥39,088 per night from Nov 5 to Nov 6
￥39,088
￥48,709 total
Nov 5 - Nov 6
includes taxes & fees
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
9.4/10 Exceptional! (1,002 reviews)
"Fantastic stay. Will return."
Reviewed on Oct 3, 2025
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.
Other neighborhoods around The Heights
Hay Beach
Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.
