The Heights Travel Guide
Tourist Guide
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.
Our pick of the best The Heights Hotel Deals
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is NZ$324 per night from 21 May to 22 May
NZ$324
21 May - 22 May
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 ...
9.6/10 Exceptional! (496 reviews)
Great for dogs - huge fenced yard
Reviewed on 11 May 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is NZ$894 per night from 2 June to 3 June
NZ$894
2 June - 3 June
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! (646 reviews)
They charged us for parking in front of our room. Unbelievable. We stayed there in April, off season, the motel was empty.
Reviewed on 11 May 2026
Sag Harbor Inn
45 West Water Street Sag Harbor NY
The price is NZ$605 per night from 3 June to 4 June
NZ$605
3 June - 4 June
includes taxes & fees
Stay at this business-friendly hotel in Sag Harbor. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (611 reviews)
Great location, seemed a little outdated for the area. Breakfast was so so, didn't seem fresh. Late check-in was very helpful.
Reviewed on 10 May 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is NZ$149 per night from 19 May to 20 May
NZ$149
19 May - 20 May
includes taxes & fees
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. ...
8/10 Very Good! (1,001 reviews)
The problem is that you can hear everything in all of the rooms above and to the right and left of you. I had a room on the first floor. I could hear every door shut, every step taken above me, and and most every conversation going on around me. It's a cute little place not far from the town center ...
Reviewed on 11 May 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is NZ$462 per night from 20 May to 21 May
NZ$462
20 May - 21 May
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 views from the restaurant and bar area. Staff were very friendly and attentive. Will stay here again.
Reviewed on 8 May 2026
The Harbor Front Inn
209 Front St Greenport NY
The price is NZ$785 per night from 10 June to 11 June
NZ$785
10 June - 11 June
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! (597 reviews)
We made our reservation paid the bill we got to the hotel they told us you have to pay $29 a night to park your car in the hotel parking lot. WE WERE NEVER INFORMED OF THIS!! I have my reservation to prove it!!!
Reviewed on 11 May 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.
