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.
The Heights Hotel Deals
The Chequit
23 Grand Ave, Shelter Island Heights, NY
The price is ₩547,143 per night from Oct 5 to Oct 6
₩547,143
₩625,110 total
Oct 5 - Oct 6
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! (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
Fully refundableReserve now, pay when you stay
The price is ₩112,918 per night from Sep 30 to Oct 1
₩112,918
₩129,863 total
Sep 30 - Oct 1
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! (1,004 reviews)
"Property was a little dated, but very comfortable. The staff was terrific."
Reviewed on Sep 27, 2025
Sound View Greenport
58775 County Rd 48, Greenport, NY
The price is ₩349,847 per night from Oct 27 to Oct 28
₩349,847
₩468,691 total
Oct 27 - Oct 28
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
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
The price is ₩137,799 per night from Oct 13 to Oct 14
₩137,799
₩158,469 total
Oct 13 - Oct 14
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! (1,009 reviews)
"Clean, quiet, friendly staff."
Reviewed on Sep 23, 2025
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
The price is ₩494,651 per night from Oct 14 to Oct 15
₩494,651
₩604,092 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! (1,013 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
The Atlantic Hotel
1655 County Road 39, Southampton, NY
The price is ₩214,417 per night from Oct 5 to Oct 6
₩214,417
₩280,214 total
Oct 5 - Oct 6
includes taxes & 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! (941 reviews)
"Clean"
Reviewed on Sep 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 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.
