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
฿6,494
per adult
Half Day(PM) North Fork Private Wine & Food Tour by Local Expert
฿14,398
per adult
Private Vacation Photoshoot with Photographer The Hamptons
฿9,364
per adult
Top hotels in The Heights
The Chequit
23 Grand Ave Shelter Island Heights NY
The price is ฿6,927 per night from 31 Oct to 1 Nov
฿6,927
฿7,914 total
31 Oct - 1 Nov
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! (64 reviews)
"The only real problem was the constant loud noise of air rushing outside the room from an air shaft along side the chimney. The staff was not able to quiet it. Most of the noise came in via the window a/c unit so removing it and closing the window would have helped. There refrigerator was warm when ..."
Reviewed on 27 Sept 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is ฿2,626 per night from 1 Oct to 2 Oct
฿2,626
฿3,020 total
1 Oct - 2 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. ...
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ฿6,020 per night from 4 Oct to 5 Oct
฿6,020
฿7,502 total
4 Oct - 5 Oct
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! (1,013 reviews)
"I felt very comfortable and at ease. I had planned on getting a massage, but never made it. Next time I will book one. The beds were comfortable. The food was good, I enjoyed myself."
Reviewed on 29 Sept 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿8,312 per night from 6 Oct to 7 Oct
฿8,312
฿10,456 total
6 Oct - 7 Oct
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 ...
The Atlantic Hotel
1655 County Road 39 Southampton NY
The price is ฿2,997 per night from 28 Oct to 29 Oct
฿2,997
฿4,264 total
28 Oct - 29 Oct
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 ...
Zey Hotel
439 Main Street Greenport NY
The price is ฿5,667 per night from 4 Oct to 5 Oct
฿5,667
฿6,475 total
4 Oct - 5 Oct
includes taxes & fees
Stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on-site and daily housekeeping. Popular attractions Greenport Harbor Brewing Company ...
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 Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.
