Visit The Heights
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
4.5/5(9 reviews)
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
4.5/5(4 reviews)
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
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
$179
per adult
76% of travellers recommend
The Heights Hotel Deals
The Chequit
23 Grand Ave Shelter Island Heights NY
Stay at this hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Shelter Island Country Club and Sunset ...
8.8/10 Excellent! (37 reviews)
A cozy room with great pillows and quiet. Perfect little place.
Reviewed on Oct 10, 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
$101 nightly
The price is $116 total per night from Nov 30 to Dec 1
$116 total
Nov 30 - Dec 1
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! (1,007 reviews)
Staff was kind. Easy, comfortable stay.
Reviewed on Nov 19, 2025
Sound View Greenport
58775 County Rd 48 Greenport NY
$199 nightly
The price is $227 total per night from Dec 18 to Dec 19
$227 total
Dec 18 - Dec 19
Total with taxes and fees
Book a stay at this 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! (593 reviews)
Amazing views and comfy bed and room. No sound privacy between the rooms at all! I guess they o relooked sound insulation in an otherwise gorgeous renovation of a roadside motel.
Reviewed on Nov 19, 2025
Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
$253 nightly
The price is $291 total per night from Nov 30 to Dec 1
$291 total
Nov 30 - Dec 1
Total with taxes and fees
Book a stay at this 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! (1,005 reviews)
Everything and everyone was fabulous!
Reviewed on Nov 19, 2025
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
$169 nightly
The price is $195 total per night from Dec 17 to Dec 18
$195 total
Dec 17 - Dec 18
Total with taxes and fees
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,004 reviews)
The rooms were clean staff were great the place wonderful we love it
Reviewed on Nov 9, 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
$75 nightly
The price is $87 total per night from Dec 24 to Dec 25
$87 total
Dec 24 - Dec 25
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! (1,000 reviews)
The room was very clean with soft towels. The sheets were clean but a bit rougher than I'm used to (I like silky sheets, not rough cotton) but the bed was comfortable and warm. The staff is very friendly too. A nice "basic" room that took care of our needs, didn't gross me out with smell or dirt ...
Reviewed on Nov 3, 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.