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
Private Vacation Photoshoot with Photographer in The Hamptons
RM1,179
per adult
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 RM742 per night from 23 Dec to 24 Dec
RM742
RM924 total
23 Dec - 24 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! (1,005 reviews)
Holiday family tradition!
Reviewed on 12 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! (1,003 reviews)
Nice, pet friendly facility with an amazing Indian restaurant next door!
Reviewed on 14 Dec 2025
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is RM510 per night from 4 Jan to 5 Jan
RM510
RM587 total
4 Jan - 5 Jan 2026
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! (396 reviews)
crystal clean, great location and PRICE! large rooms. plenty of space. absolutely amazing
Reviewed on 14 Dec 2025
Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
The price is RM1,260 per night from 23 Dec to 24 Dec
RM1,260
RM1,550 total
23 Dec - 24 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! (1,000 reviews)
Friendly and helpful staff, wonderful dining experience at Fresh Salt
Reviewed on 13 Dec 2025
Sea Crest Resort
2166 Montauk Hwy Amagansett NY
Stay at this beach hotel in Amagansett. Enjoy free Wi-Fi, a beach locale and a fitness centre. Popular attractions Walking Dunes Trailhead and Hither Hills State ...
9/10 Wonderful! (507 reviews)
Lovely, clean 1 bedroom with spectacular view
Reviewed on 13 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.
