The Heights Travel Guide
Shelter Island Heights
Visit The Heights
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 ฿6,875 per night from 4 Oct to 5 Oct
฿6,875
฿7,854 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 ...
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is ฿2,710 per night from 21 Sept to 22 Sept
฿2,710
฿3,116 total
21 Sept - 22 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)
"Room need complete makeover"
Reviewed on 15 Sept 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿8,843 per night from 1 Oct to 2 Oct
฿8,843
฿11,054 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! (727 reviews)
"A lot of money for what is a motel sitting on a major road with a popular restaurant. Have to run across the road after parking to avoid traffic. No usable chair in the room. No closet. Great shower. Nice view from the porch. Decent 8am continental breakfast. (I’d prefer coffee at 7…) Staff was helpful. ..."
Reviewed on 15 Sept 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ฿5,967 per night from 7 Oct to 8 Oct
฿5,967
฿7,436 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! (1,003 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 ฿3,970 per night from 1 Oct to 2 Oct
฿3,970
฿5,368 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! (1,007 reviews)
"I had room facing the busy street, but the room was well insulated and I did not hear the traffic from outside. Also, the floor plan was very functional. Linen was clean CLEAN, bed was SO comfortable And the amenities of small fridge, coffee maker, iron, -and 2 water bottles provided with each room ..."
Reviewed on 15 Sept 2026
Zey Hotel
439 Main Street Greenport NY
The price is ฿5,618 per night from 27 Sept to 28 Sept
฿5,618
฿6,418 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! (402 reviews)
"My Husband Phil & I had the Best Stay. Very Quaint Hotel, just a couple of blocks from waterfront.Absolutely spotless, so many sitting areas, Coffee, tea water and ice available 24-7. Our room was spotless, decorated so well. We also had a balcony. James and all staff were so Pleasant and so accommodating. ..."
Reviewed on 14 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.
