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
CA $218
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
CA $187
per adult
The Heights Hotel Deals
The Chequit
23 Grand Ave, Shelter Island Heights, NY
The price is CA $721 per night from Jul 27 to Jul 28
CA $721
CA $824 total
Jul 27 - Jul 28
includes taxes & 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! (31 reviews)
"we loved it!"
Reviewed on Jul. 9, 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
The price is CA $150 per night from Aug 3 to Aug 4
CA $150
CA $173 total
Aug 3 - Aug 4
includes taxes & 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! (1,006 reviews)
"Just a little tired looking, but very nice staff. Everything went well. Thank you. Good value for everything."
Reviewed on Jul. 21, 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
The price is CA $109 per night from Jul 27 to Jul 28
CA $109
CA $125 total
Jul 27 - Jul 28
includes taxes & 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. ...
7.6/10 Good! (1,001 reviews)
"Very convenient to the beaches and very clean room. I had some trouble with the door lock but nothing major. I'm a doofus. Will definitely return."
Reviewed on Jul. 16, 2025
Sound View Greenport
58775 County Rd 48, Greenport, NY
The price is CA $630 per night from Aug 21 to Aug 22
CA $630
CA $790 total
Aug 21 - Aug 22
includes taxes & 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! (541 reviews)
"Every room comes with an ocean view, steps down to the beach. Activities at night. Band at the ocean on certain nights. Will be back every year! Help with bags and getting to room by golf cart."
Reviewed on Jul. 22, 2025
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
The price is CA $478 per night from Aug 12 to Aug 13
CA $478
CA $577 total
Aug 12 - Aug 13
includes taxes & 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! (1,007 reviews)
"Rooms were large and spacious but quite dark. The Choo Choo lounge and the outside bar were very pleasant. The onsite dining restaurant was disappointing, food was below expectations and did not live up to their rating. Staff were all very pleasant. Parking was a difficult but it is high season."
Reviewed on Jul. 21, 2025
The Atlantic Hotel
1655 County Road 39, Southampton, NY
The price is CA $342 per night from Aug 3 to Aug 4
CA $342
CA $424 total
Aug 3 - Aug 4
includes taxes & fees
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
7/10 Good! (883 reviews)
Yes
"Great"
Reviewed on Jul. 23, 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
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.