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.
Top hotels in The Heights
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is Rp4.069.670 per night from 20 Apr to 21 Apr
Rp4.069.670
Rp4.975.164 total
20 Apr - 21 Apr
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! (1,007 reviews)
Front desk staff were amazing! The bar staff were very attentive and friendly. Rooms are clean, but definitely dated.
Reviewed on 13 Apr 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is Rp2.635.992 per night from 3 May to 4 May
Rp2.635.992
Rp4.477.263 total
3 May - 4 May
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! (632 reviews)
Loved our stay. Our room was gorgeous a s in the perfect location. Would recommend and plan on coming back in the future!
Reviewed on 12 Apr 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is Rp2.717.795 per night from 19 Apr to 20 Apr
Rp2.717.795
Rp3.122.185 total
19 Apr - 20 Apr
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! (459 reviews)
Incredible room
Reviewed on 13 Apr 2026
The Harbor Front Inn
209 Front St Greenport NY
The price is Rp3.063.326 per night from 27 Apr to 28 Apr
Rp3.063.326
Rp3.988.340 total
27 Apr - 28 Apr
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! (583 reviews)
Lovely place for a quiet getaway off-season. Loved this place and will be back. Only disappointment was morning coffee … lacking flavor and lukewarm … but there is a wonderful shop just a few doors down with very good coffee. Nespresso machine in room.
Reviewed on 13 Apr 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is Rp1.158.780 per night from 15 Apr to 16 Apr
Rp1.158.780
Rp1.332.597 total
15 Apr - 16 Apr
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)
Great place to stay on the shoreline. Privately owned so you.are supporting local businesses!
Reviewed on 10 Apr 2026
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is Rp3.217.262 per night from 27 Apr to 28 Apr
Rp3.217.262
Rp4.103.322 total
27 Apr - 28 Apr
includes taxes & fees
Stay at this hotel in Southold. Enjoy free Wi-Fi, free bicycles on-site and a business centre. Our guests praise the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (260 reviews)
Beautiful space in Southold
Reviewed on 11 Apr 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.
