The Heights
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 carefree afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
Crescent Beach
Why not spend a carefree afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
Things to do
Private Vacation Photoshoot with Photographer in The Hamptons
P17,248
per adult
Top hotels in The Heights
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is P9,775 per night from May 17 to May 18
P9,775
P11,168 total
May 17 - May 18
includes taxes & fees
Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (496 reviews)
Great for dogs - huge fenced yard
Reviewed on May 11, 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is P17,881 per night from May 26 to May 27
P17,881
P25,668 total
May 26 - May 27
includes taxes & fees
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
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 May 11, 2026
Sag Harbor Inn
45 West Water Street Sag Harbor NY
Fully refundableReserve now, pay when you stay
The price is P19,257 per night from Jun 4 to Jun 5
P19,257
P22,001 total
Jun 4 - Jun 5
includes taxes & fees
Book a stay at this business-friendly hotel in Sag Harbor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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Great location, seemed a little outdated for the area.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 May 10, 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is P4,736 per night from May 19 to May 20
P4,736
P5,446 total
May 19 - May 20
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our 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 May 11, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is P13,777 per night from May 20 to May 21
P13,777
P16,905 total
May 20 - May 21
includes taxes & fees
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
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 May 8, 2026
The Harbor Front Inn
209 Front St Greenport NY
The price is P17,651 per night from May 21 to May 22
P17,651
P23,326 total
May 21 - May 22
includes taxes & fees
Book a stay at this business-friendly hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
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 May 11, 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.
