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 carefree afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
Crescent Beach
Why not spend a carefree afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
Things to do
Long Island Wine and Food Day Trip with Sommelier host from NYC
$148
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
$139
per adult
The Heights Hotel Deals
The Chequit
23 Grand Ave, Shelter Island Heights, NY
$282 nightly
The price is $323 total per night from Nov 2 to Nov 3
$323 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this 3-star hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Shelter Island Country Club and ...
8.8/10 Excellent! (36 reviews)
"Always a sold stay on Shelter Island"
Reviewed on Aug 23, 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
$83 nightly
The price is $96 total per night from Oct 7 to Oct 8
$96 total
Oct 7 - Oct 8
Total with taxes and fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.8/10 Good! (1,004 reviews)
"Property was a little dated, but very comfortable. The staff was terrific."
Reviewed on Sep 27, 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
$94 nightly
The price is $108 total per night from Nov 2 to Nov 3
$108 total
Nov 2 - Nov 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,012 reviews)
"We have stayed there before so have been pleased with it."
Reviewed on Sep 29, 2025
Sound View Greenport
58775 County Rd 48, Greenport, NY
$291 nightly
The price is $332 total per night from Oct 27 to Oct 28
$332 total
Oct 27 - Oct 28
Total with taxes and fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (574 reviews)
"Clean and beautiful view"
Reviewed on Sep 16, 2025
The Atlantic Hotel
1655 County Road 39, Southampton, NY
$138 nightly
The price is $158 total per night from Nov 2 to Nov 3
$158 total
Nov 2 - Nov 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Southampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7/10 Good! (944 reviews)
"Really more of a motel not a hotel. Room was basic but adequate and clean. Close to Southampton. They were fully booked on one of the weekend days of our stay so rate that night was high for this type of lodging."
Reviewed on Sep 30, 2025
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
$331 nightly
The price is $380 total per night from Nov 2 to Nov 3
$380 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
9.4/10 Exceptional! (1,013 reviews)
"My husband used the spa and said it was excellent. The housekeeping staff was generally good - -forgot some tasks a couple of times. Front of the house staff excellent. Special shoutout to Jack!! Very surprised that there was no inroom safe. Bathroom needs a remodel -needs taller counters…as well ..."
Reviewed on Sep 26, 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 neighborhoods around The Heights
Hay Beach
Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.
