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 $744 per night from Aug 14 to Aug 15
CA $744
CA $850 total
Aug 14 - Aug 15
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 ...
8.6/10 Excellent! (30 reviews)
"we loved it!"
Reviewed on Jul. 9, 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
The price is CA $151 per night from Aug 3 to Aug 4
CA $151
CA $174 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! (1,008 reviews)
Excellent Place to Stay!!!...5 Stars & More!!
"We stayed 5 days! Customer service was great ;) Housekeeping was great, the cafe in the morning was excellent! Lounge area if you wanted to go out in the evening they had Pool, Darts, & Karaoke If you didn't want to go to the Beach, they had a Pool/Gym Right near the Highway & Route 1 We had a wonderful ..."
Reviewed on Jul. 10, 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
The price is CA $110 per night from Jul 20 to Jul 21
CA $110
CA $126 total
Jul 20 - Jul 21
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! (992 reviews)
"The roadside in exceeded my expectations in all areas"
Reviewed on Jul. 9, 2025
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
The price is CA $492 per night from Jul 16 to Jul 17
CA $492
CA $593 total
Jul 16 - Jul 17
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! (1,004 reviews)
"Fantastic!! Loved staying at this luxurious hotel"
Reviewed on Jul. 8, 2025
The Atlantic Hotel
1655 County Road 39, Southampton, NY
The price is CA $344 per night from Jul 20 to Jul 21
CA $344
CA $427 total
Jul 20 - Jul 21
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! (875 reviews)
"The staff was very welcoming. The room was clean and very spacious. The location is great. Would highly recommend."
Reviewed on Jul. 14, 2025
Baron's Cove
31 West Water Street, Sag Harbor, NY
The price is CA $690 per night from Jul 16 to Jul 17
CA $690
CA $867 total
Jul 16 - Jul 17
includes taxes & fees
Stay at this 4-star hotel in Sag Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (264 reviews)
"Really beautiful and clean property that is very convenient and great amenities."
Reviewed on Jun. 27, 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.