The Heights Travel Guide
Shelter Island Heights
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
Long Island Wine Tour North Fork Sights Bites Flights Half Day PM
฿10,664
per adult
Top hotels in The Heights
House on Chase Creek
3 Locust Avenue Shelter Island Heights NY
The price is ฿3,235 per night from 26 Jan to 27 Jan
฿3,235
฿3,697 total
26 Jan - 27 Jan
includes taxes & fees
Stay at this golf guesthouse in Shelter Island Heights. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Popular attractions Shelter Island Country Club ...
9.4/10 Exceptional! (79 reviews)
The House on Chase Creek is absolutely amazing! My husband and I are celebrating our 20th anniversary and I’ve been telling him about Shelter Island literally for almost 40 years. Well we finally made it and the trip, the home, the welcoming of my dog, was all so just so welcoming and nice. Bill, ...
Reviewed on 9 Nov 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! (1,002 reviews)
I have stayed here a number of times, and each time the room has been spotless and smells fresh. The staff is very friendly and always offers to help in some way, whether it's to get the snow off my car or provide bottled water. I will be staying here again!
Reviewed on 23 Jan 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿4,167 per night from 26 Jan to 27 Jan
฿4,167
฿5,649 total
26 Jan - 27 Jan
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! (607 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...
Reviewed on 10 Jan 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ฿6,072 per night from 2 Feb to 3 Feb
฿6,072
฿7,518 total
2 Feb - 3 Feb
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! (1,002 reviews)
Great room and staff
Reviewed on 14 Jan 2026
The Atlantic Hotel
1655 County Road 39 Southampton NY
Stay at this hotel in Southampton. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
7/10 Good! (978 reviews)
Staff was very friendly room was clean and comfortable
Reviewed on 11 Jan 2026
The Harbor Front Inn
209 Front St Greenport NY
The price is ฿3,640 per night from 27 Jan to 28 Jan
฿3,640
฿5,047 total
27 Jan - 28 Jan
includes taxes & fees
Stay at this business-friendly hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (562 reviews)
The staff was wonderful and the room and views fantastic.
Reviewed on 12 Jan 2026
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.
