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
฿6,611
per adult
Half Day(PM) North Fork Private Wine & Food Tour by Local Expert
฿14,657
per adult
Private Vacation Photoshoot with Photographer The Hamptons
฿9,317
per adult
Top hotels in The Heights
The Chequit
23 Grand Ave Shelter Island Heights NY
The price is ฿6,019 per night from 1 Nov to 2 Nov
฿6,019
฿6,877 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 ...
9/10 Wonderful! (71 reviews)
"Terrible experience."
Reviewed on 22 Oct 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ฿6,320 per night from 1 Nov to 2 Nov
฿6,320
฿7,848 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! (1,001 reviews)
"Great"
Reviewed on 21 Oct 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is ฿2,746 per night from 15 Nov to 16 Nov
฿2,746
฿3,157 total
15 Nov - 16 Nov
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! (1,001 reviews)
"I stayed twice and borh rooms were decorated uniquely. The staff and owners were very nice. Good people"
Reviewed on 21 Oct 2026
The Atlantic Hotel
1655 County Road 39 Southampton NY
The price is ฿3,599 per night from 28 Oct to 29 Oct
฿3,599
฿4,952 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 ...
7.2/10 Good! (1,000 reviews)
"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"
Reviewed on 19 Oct 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿5,821 per night from 22 Nov to 23 Nov
฿5,821
฿7,611 total
22 Nov - 23 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 ฿6,124 per night from 26 Oct to 27 Oct
฿6,124
฿6,996 total
26 Oct - 27 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! (435 reviews)
"The hotel had a good vibe and energy! Lots of artwork and was very charming. It has a bed and breakfast feel to it. The parking is behind the hotel and free and convenient. It’s right on Main Street and walking distance to all restaurants and bars. The staff especially James was warm and friendly ..."
Reviewed on 22 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.
