The Heights Travel Guide
Shelter Island Heights
Visit The Heights
Stay near popular The Heights attractions
Things to do
Private Luxury Wine Tours of Long Island Pindar Winery
฿6,552
per adult
Half Day(PM) North Fork Private Wine & Food Tour by Local Expert
฿14,527
per adult
Top hotels in The Heights
The Chequit
23 Grand Ave Shelter Island Heights NY
The price is ฿9,615 per night from 8 Sept to 9 Sept
฿9,615
฿10,986 total
8 Sept - 9 Sept
includes taxes & fees
Stay at this hotel in Shelter Island Heights. Enjoy free Wi-Fi, free parking and premium bedding. Popular attractions Shelter Island Country Club and Sunset ...
9.2/10 Wonderful! (52 reviews)
"pretty and clean!"
Reviewed on 25 Aug 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿9,710 per night from 15 Sept to 16 Sept
฿9,710
฿13,931 total
15 Sept - 16 Sept
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 ...
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is ฿2,866 per night from 30 Aug to 31 Aug
฿2,866
฿3,296 total
30 Aug - 31 Aug
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)
"My room smelled like urine and the lobby smelled like a wet dog. Bathroom was dim and dingy, ironing board stained, A/C vents were full of dust and didn’t work well. TV didn’t work either. How they can charge $150 for a room here is appalling. The front sign is the only thing nice about the property- ..."
Reviewed on 28 Aug 2026
The Atlantic Hotel
1655 County Road 39 Southampton NY
The price is ฿5,930 per night from 28 Sept to 29 Sept
฿5,930
฿7,603 total
28 Sept - 29 Sept
includes taxes & fees
Stay at this hotel in Southampton. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
7.2/10 Good! (1,000 reviews)
"This hotel is a dump and needs a complete overhaul. The paint is peeling the bathrooms are miniature and toilets don’t work. There is no maid service and they lie on their ad about taking guests to the shore it really should be torn down."
Reviewed on 25 Aug 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ฿7,663 per night from 14 Sept to 15 Sept
฿7,663
฿9,379 total
14 Sept - 15 Sept
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 ...
North Fork Resort
690 Queen St Greenport NY
The price is ฿11,736 per night from 7 Sept to 8 Sept
฿11,736
฿13,408 total
7 Sept - 8 Sept
includes taxes & fees
Stay at this cottage in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
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.
Where to stay in The Heights
Find the best The Heights areas for the activities you enjoy most.
Hay Beach
When in Hay Beach, you can plan a visit to Greenport Carousel and Greenport Harbor Brewing Company, some noteworthy sights in the nearby area.
