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
Fully refundableReserve now, pay when you stay
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! (1,006 reviews)
Beautiful property on the water! Loved it! Only problem was the noisy air handler!
Reviewed on 12 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 Rp2.375.839 per night from 27 Apr to 28 Apr
Rp2.375.839
Rp2.731.500 total
27 Apr - 28 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 Rp2.532.140 per night from 15 Apr to 16 Apr
Rp2.532.140
Rp3.381.460 total
15 Apr - 16 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! (582 reviews)
Everything was so
Reviewed on 11 Apr 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is Rp1.239.185 per night from 14 Apr to 15 Apr
Rp1.239.185
Rp1.425.105 total
14 Apr - 15 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 Rp2.895.536 per night from 30 Apr to 1 May
Rp2.895.536
Rp3.735.751 total
30 Apr - 1 May
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! (259 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.
