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
Top hotels in The Heights
The Chequit
23 Grand Ave Shelter Island Heights NY
The price is ฿6,897 per night from 4 Oct to 5 Oct
฿6,897
฿7,880 total
4 Oct - 5 Oct
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! (59 reviews)
"Amazing!! staff were lovely and hotel is so clean and so pretty"
Reviewed on 16 Sept 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is ฿2,715 per night from 22 Sept to 23 Sept
฿2,715
฿3,123 total
22 Sept - 23 Sept
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! (1,003 reviews)
"Staff was helpful and professional. Room was clean, basic, nice. The TV was a little sketchy-some stations were static. The bathroom shower was great: good flow, hot and soothing. Overall, very good for the price."
Reviewed on 17 Sept 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿8,851 per night from 14 Oct to 15 Oct
฿8,851
฿11,064 total
14 Oct - 15 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 ...
8.4/10 Very good! (731 reviews)
"Nice property clean rooms unique having room right on the ocean front was surprised by a pretty nice breakfast many choices food coffee which is always important overall the property is well located to visit surrounding farms and vineyards and short car ride to restaurants and water front"
Reviewed on 19 Sept 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ฿5,973 per night from 7 Oct to 8 Oct
฿5,973
฿7,443 total
7 Oct - 8 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! (1,000 reviews)
"It was the perfect getaway- close to home. The property was beautiful, clean and peaceful. The beach could have been cleaner, but overall we loved our stay. The food served in their variety of restaurants was delicious. We will definitely return."
Reviewed on 15 Sept 2026
The Atlantic Hotel
1655 County Road 39 Southampton NY
The price is ฿3,973 per night from 1 Oct to 2 Oct
฿3,973
฿5,373 total
1 Oct - 2 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 ...
7.2/10 Good! (1,001 reviews)
"Bed, floor not very clean; Room… walls, furniture, doors cracked, broken, chipped. Walking from lot to back of bldg where room was located, there was no exterior light so felt dangerous. Can hear every footstep from room above so impossible to sleep when people were still walking around middle of ..."
Reviewed on 18 Sept 2026
Zey Hotel
439 Main Street Greenport NY
The price is ฿5,623 per night from 27 Sept to 28 Sept
฿5,623
฿6,424 total
27 Sept - 28 Sept
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! (405 reviews)
"Very pleasant layout, center of town. Common areas are beautiful plus Hakan Bey is very helpful and accommodating"
Reviewed on 18 Sept 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 Greenport Carousel and Greenport Harbor Brewing Company, some noteworthy sights in the nearby area.
