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
Long Island Wine and Food Day Trip with Sommelier host from NYC
฿4,716
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
฿4,429
per adult
Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM
฿10,802
per adult
Top hotels in The Heights
The Chequit
23 Grand Ave, Shelter Island Heights, NY
Stay at this 3-star hotel in Shelter Island Heights. Enjoy free Wi-Fi, 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 23 Aug 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
The price is ฿2,591 per night from 8 Oct to 9 Oct
฿2,591
฿2,979 total
8 Oct - 9 Oct
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. ...
7.8/10 Good! (1,005 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 4 Oct 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
The price is ฿3,034 per night from 2 Nov to 3 Nov
฿3,034
฿3,489 total
2 Nov - 3 Nov
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 ...
7.6/10 Good! (1,005 reviews)
"Overall, a nice hotel for a one day trip! :)"
Reviewed on 5 Oct 2025
Sound View Greenport
58775 County Rd 48, Greenport, NY
The price is ฿7,680 per night from 21 Oct to 22 Oct
฿7,680
฿10,363 total
21 Oct - 22 Oct
includes taxes & fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
8.4/10 Very Good! (577 reviews)
"Nice views on sunset"
Reviewed on 3 Oct 2025
The Atlantic Hotel
1655 County Road 39, Southampton, NY
Stay at this business-friendly hotel in Southampton. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
7/10 Good! (948 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 30 Sept 2025
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
The price is ฿8,439 per night from 5 Nov to 6 Nov
฿8,439
฿10,516 total
5 Nov - 6 Nov
includes taxes & fees
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
9.4/10 Exceptional! (1,005 reviews)
"Relaxing wonderful staff!"
Reviewed on 6 Oct 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 neighbourhoods around The Heights
Hay Beach
When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.
