The Heights Travel Guide
Shelter Island Heights
Visit The Heights
Stay near popular The Heights attractions
Things to do
Half-Day Private Long Island Wine Tour Experience
฿9,517
per adult
Private Luxury Wine Tours of Long Island Pindar Winery
฿6,494
per adult
Top hotels in The Heights
The Chequit
23 Grand Ave Shelter Island Heights NY
The price is ฿6,811 per night from 4 Oct to 5 Oct
฿6,811
฿7,782 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! (57 reviews)
"Good location , bar was nice and fire pits"
Reviewed on 9 Sept 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿8,738 per night from 1 Oct to 2 Oct
฿8,738
฿10,922 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 ...
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is ฿2,716 per night from 10 Sept to 11 Sept
฿2,716
฿3,124 total
10 Sept - 11 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)
"Welcoming, helpful, friendly, professional front desk staff. My room was impeccably clean and tidy. The property is centrally-located with ease of accessibility to main roads and major highways, yet far enough off Boston Post Road to ensure a quiet, peaceful and restful stay. Overall, an outstanding, ..."
Reviewed on 8 Sept 2026
The Atlantic Hotel
1655 County Road 39 Southampton NY
The price is ฿3,924 per night from 1 Oct to 2 Oct
฿3,924
฿5,306 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! (1,013 reviews)
"Getting my key card was easy enough but getting the lock box to close was a pain. Jetted tub didn't blow any bubbles. The bed was uncomfortable and I got woken up by my neighbors when they came in from the bar. The room was clean but the back of the front door was pretty dirty. Over all I will give ..."
Reviewed on 9 Sept 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ฿5,898 per night from 7 Oct to 8 Oct
฿5,898
฿7,350 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 ...
Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
The price is ฿11,484 per night from 4 Oct to 5 Oct
฿11,484
฿14,358 total
4 Oct - 5 Oct
includes taxes & fees
Stay at this spa hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in their reviews. ...
9.6/10 Exceptional! (1,008 reviews)
"Old Saybrook never disappoints. The rooms have been remodel Edinburgh the last six months but the resort has managed to retain its old world chatm. Eventhough there were three weddings at the property during our visit, the staff were attentive to us and we weren't as re remained their only guests. ..."
Reviewed on 7 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.
