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
￥28,176
per adult
76% of travellers recommend
Private Vacation Photoshoot with Photographer in The Hamptons
￥40,465
per adult
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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
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! (1,003 reviews)
Friendly. Had to check in early and was walked to our room so we knew exactly where it was gif when we returned later.
Reviewed on Nov 28, 2025
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ￥24,785 per night from Dec 3 to Dec 4
￥24,785
￥31,198 total
Dec 3 - Dec 4
includes taxes & 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! (1,007 reviews)
Staff is fantastic
Reviewed on Nov 24, 2025
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ￥25,035 per night from Dec 1 to Dec 2
￥25,035
￥36,246 total
Dec 1 - Dec 2
includes taxes & 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
Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
The price is ￥15,798 per night from Dec 7 to Dec 8
￥15,798
￥18,167 total
Dec 7 - Dec 8
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! (1,010 reviews)
Great
Reviewed on Nov 24, 2025
Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
The price is ￥43,918 per night from Dec 17 to Dec 18
￥43,918
￥54,411 total
Dec 17 - Dec 18
includes taxes & 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! (1,008 reviews)
Lovely, lovely place. Helpful and nice staff, immaculate rooms. Excellent on site restaurant, Fresh Salt. Great location.
Reviewed on Nov 25, 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.
