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 ฿8,113 per night from 8 Sept to 9 Sept
฿8,113
฿9,269 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 ...
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿8,083 per night from 1 Oct to 2 Oct
฿8,083
฿10,182 total
1 Oct - 2 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! (712 reviews)
"I booked thru Expedia but never checked in because you were SOLD OUzt! Expedia has a problem to fix!"
Reviewed on 2 Sept 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is ฿3,048 per night from 13 Sept to 14 Sept
฿3,048
฿3,506 total
13 Sept - 14 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! (1,000 reviews)
"Reasonable price, nice staff, clean rooms. Fills the need for a short stay!"
Reviewed on 1 Sept 2026
The Atlantic Hotel
1655 County Road 39 Southampton NY
The price is ฿3,969 per night from 1 Oct to 2 Oct
฿3,969
฿5,367 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 ...
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ฿6,442 per night from 21 Sept to 22 Sept
฿6,442
฿7,980 total
21 Sept - 22 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 ...
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is ฿5,059 per night from 20 Sept to 21 Sept
฿5,059
฿6,612 total
20 Sept - 21 Sept
includes taxes & fees
Stay at this business-friendly hotel in Southampton. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (573 reviews)
"A well thought out space. Staff is welcoming and helpful. The Room met our expectations. They even offer a beach pass for the Southampton town beach!"
Reviewed on 31 Aug 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.
