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
￥21,679
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
￥21,972
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
￥20,636
per adult
The Heights Hotel Deals
The Chequit
23 Grand Ave, Shelter Island Heights, NY
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
The price is ￥11,920 per night from Sep 28 to Sep 29
￥11,920
￥13,709 total
Sep 28 - Sep 29
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. ...
7.8/10 Good! (1,011 reviews)
"Highly recommend!"
Reviewed on Sep 21, 2025
Sound View Greenport
58775 County Rd 48, Greenport, NY
The price is ￥38,167 per night from Oct 26 to Oct 27
￥38,167
￥50,889 total
Oct 26 - Oct 27
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! (572 reviews)
"Clean and beautiful view"
Reviewed on Sep 16, 2025
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is ￥52,219 per night from Oct 14 to Oct 15
￥52,219
￥63,772 total
Oct 14 - Oct 15
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! (1,010 reviews)
"Loved everything about this property. Location, Staff, Amenities. Decor and furniture beautiful."
Reviewed on Sep 24, 2025
The Atlantic Hotel
1655 County Road 39, Southampton, NY
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! (941 reviews)
"Clean"
Reviewed on Sep 23, 2025
The Bentley Hotel Southampton
161 Hills Station Rd, Southampton, NY
The price is ￥26,437 per night from Oct 1 to Oct 2
￥26,437
￥30,205 total
Oct 1 - Oct 2
includes taxes & fees
Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (341 reviews)
"Huge second floor suite. Full size fridge freezer and microwave. Excellent shower. Super comfortable beds. All spotlessly clean. Added bonus of an outdoor pool. Would not hesitate to stay in this hotel again."
Reviewed on Sep 24, 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.
