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
Why not spend a care-free afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
Crescent Beach
Why not spend a care-free afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
Things to do
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
€154
per adult
76% of travellers recommend
Top hotels in The Heights
The Chequit
23 Grand Ave Shelter Island Heights NY
Stay at this hotel in Shelter Island Heights. Enjoy free Wi-Fi, 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 10 Oct 2025
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is €178 per night from 16 Dec to 17 Dec
€178
16 Dec - 17 Dec
includes taxes & fees
Stay at this beach resort in Westbrook. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.8/10 Excellent! (1,003 reviews)
The staff were all pleasant and helpful. View from the room was amazing. Place was decorated beautifully for Christmas. Beautiful wood burning fireplaces to sit by and relax. The perfect cold weather getaway
Reviewed on 10 Dec 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
7.8/10 Good! (1,000 reviews)
The staff couldn’t have been nicer! Courteous and caring. The room was immaculate with all necessary amenities. Somewhat dated but not shabby. Very close to town. Parking was ample and right outside my door! I attended a concert at the Kate and did not want to drive an hour home late that evening, ...
Reviewed on 7 Dec 2025
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is €206 per night from 13 Jan to 14 Jan
€206
13 Jan - 14 Jan 2026
includes taxes & fees
Stay at this beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.4/10 Very Good! (598 reviews)
Great room with amazing views! Staff was fantastic and the food was great too
Reviewed on 28 Nov 2025
Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
The price is €324 per night from 15 Dec to 16 Dec
€324
15 Dec - 16 Dec
includes taxes & fees
Stay at this spa hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in their reviews. ...
9.4/10 Exceptional! (1,002 reviews)
My stay with Saybrook Point Resort & Marina was amazing. Clean room, amazing staff and amenities! I plan to return again!
Reviewed on 8 Dec 2025
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is €123 per night from 21 Dec to 22 Dec
€123
21 Dec - 22 Dec
includes taxes & fees
Stay at this business-friendly hotel in Southampton. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (391 reviews)
Had a wonderful stay at The Bentley Hotel Southampton. The room was spacious, stylish, and spotless. I especially loved the record player — such a unique and thoughtful touch that made the stay feel personal and relaxing. The overall vibe of the room and the layout were perfect. Staff were friendly ...
Reviewed on 7 Dec 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.
The Heights
- Cooper's Beach
- East Hampton Main Beach
- Wolffer Estates Vineyard
- Shinnecock Hills Golf Course
- Hither Hills State Park
- Orient Point County Park
- Macari Vineyards
- Guild Hall
- Hole-in-the-Wall Beach
- Shinnecock Nation Cultural Center and Museum
- Harvey's Beach
- LongHouse Reserve
- Ponquogue Beach
- Pleasure Beach
