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
฿5,818
per adult
76% of travellers recommend
Long Island Wine Tour North Fork Sights Bites Flights Half Day PM
฿11,018
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
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 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 3 Nov 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
The price is ฿3,283 per night from 30 Nov to 1 Dec
฿3,283
฿3,775 total
30 Nov - 1 Dec
includes taxes & fees
Stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7.6/10 Good! (1,007 reviews)
Staff was kind. Easy, comfortable stay.
Reviewed on 19 Nov 2025
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is ฿5,203 per night from 23 Nov to 24 Nov
฿5,203
฿7,532 total
23 Nov - 24 Nov
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! (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 19 Nov 2025
Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
Fully refundableReserve now, pay when you stay
The price is ฿7,858 per night from 30 Nov to 1 Dec
฿7,858
฿9,848 total
30 Nov - 1 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! (1,005 reviews)
Everything and everyone was fabulous!
Reviewed on 19 Nov 2025
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
The price is ฿3,609 per night from 30 Nov to 1 Dec
฿3,609
฿4,156 total
30 Nov - 1 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! (381 reviews)
Great
Reviewed on 16 Nov 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.
