Popular places to visit
Shelter Island Country Club
Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.
Sunset Beach
Why not spend a care-free afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
Crescent Beach
Why not spend a care-free afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
Things to do
Long Island Wine and Food Day Trip with Sommelier host from NYC
฿4,848
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
฿4,553
per adult
Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM
฿11,104
per adult
Top hotels in The Heights
The Chequit
23 Grand Ave, Shelter Island Heights, NY
Stay at this 3-star hotel in Shelter Island Heights. Enjoy free Wi-Fi, free parking and premium bedding. Popular attractions Shelter Island Country Club and ...
8.8/10 Excellent! (33 reviews)
"Everyone was amazing"
Reviewed on 15 Aug 2025
The Atlantic Hotel
1655 County Road 39, Southampton, NY
Stay at this business-friendly hotel in Southampton. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
7/10 Good! (913 reviews)
"Nice place. Recommend."
Reviewed on 18 Aug 2025
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
The price is ฿11,579 per night from 26 Aug to 27 Aug
฿11,579
฿13,967 total
26 Aug - 27 Aug
includes taxes & fees
Stay at this 3.5-star 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 ...
9.4/10 Exceptional! (1,004 reviews)
"The bed and pillows are the best I’ve ever slept on!! Very clean! Had a wonderful dinner at Fresh Salt. Spa was very nice and had great services."
Reviewed on 18 Aug 2025
Sound View Greenport
58775 County Rd 48, Greenport, NY
The price is ฿9,435 per night from 9 Sept to 10 Sept
฿9,435
฿12,374 total
9 Sept - 10 Sept
includes taxes & fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
8.4/10 Very Good! (560 reviews)
"Feels like a remote vacation destination just a couple of hours from home. Self-contained property with private beach and pool away from crowds and tourists, but close to town."
Reviewed on 13 Aug 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is ฿3,324 per night from 15 Sept to 16 Sept
฿3,324
฿3,822 total
15 Sept - 16 Sept
includes taxes & fees
Stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7.6/10 Good! (1,011 reviews)
"Perfect spot for my visit"
Reviewed on 17 Aug 2025
The Bentley Hotel Southampton
161 Hills Station Rd, Southampton, NY
The price is ฿7,137 per night from 9 Sept to 10 Sept
฿7,137
฿9,083 total
9 Sept - 10 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 ...
9.4/10 Exceptional! (315 reviews)
Such a gem!
"Pleasantly surprised at just how adorable this place was. Also, the room was very large!"
Reviewed on 15 Aug 2025
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.
Other neighbourhoods around The Heights
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.