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 ฿5,009 per night from 1 Nov to 2 Nov
฿5,009
฿5,722 total
1 Nov - 2 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! (65 reviews)
"Friendly staff , Unique property."
Reviewed on 4 Oct 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is ฿2,624 per night from 5 Oct to 6 Oct
฿2,624
฿3,018 total
5 Oct - 6 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. ...
8/10 Very good! (1,002 reviews)
"Nice place !"
Reviewed on 1 Oct 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ฿5,260 per night from 1 Nov to 2 Nov
฿5,260
฿6,628 total
1 Nov - 2 Nov
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! (1,000 reviews)
"The property was definitely worth a five-star rating and the views of the Bay were tremendous! The rooms were very clean and the beds were super comfortable. I had a wonderful breakfast looking out over the water. It was magical"
Reviewed on 2 Oct 2026
The Atlantic Hotel
1655 County Road 39 Southampton NY
The price is ฿2,995 per night from 28 Oct to 29 Oct
฿2,995
฿4,261 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 ...
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿6,434 per night from 2 Nov to 3 Nov
฿6,434
฿8,310 total
2 Nov - 3 Nov
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 ...
Zey Hotel
439 Main Street Greenport NY
The price is ฿5,663 per night from 5 Oct to 6 Oct
฿5,663
฿6,470 total
5 Oct - 6 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 ...
9.2/10 Wonderful! (419 reviews)
"Our stay was impressive. We hadn't expected how comfortable and roomy the suite was. The whirlpool bath was like a small swimming pool and the room was large enough to have a party."
Reviewed on 3 Oct 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.
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.
