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 6.267.255 ₫ per night from 22 Apr to 23 Apr
6.267.255 ₫
7.661.709 ₫ total
22 Apr - 23 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 4.059.404 ₫ per night from 3 May to 4 May
4.059.404 ₫
6.894.945 ₫ 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! (633 reviews)
We love the Sound View. As a school social worker, I sometimes REALLY need to reset. There is no better place to do it than here with the most amazing views! We have been coming 3x a year with our pup. Great staff and restaurant! The hotel really tries to accommodate requests, such as a certain room ...
Reviewed on 14 Apr 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is 3.740.280 ₫ per night from 30 Apr to 1 May
3.740.280 ₫
4.299.609 ₫ total
30 Apr - 1 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! (461 reviews)
This hotel was lovely. I enjoyed the decor, how spacious it was, the lawn and the couches to sit in outside. Truly, an amazing experience in every way. The staff was always welcoming and helpful. No complaints and I would definitely stay again if I come to the Hamptons!
Reviewed on 13 Apr 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is 2.149.081 ₫ per night from 21 Apr to 22 Apr
2.149.081 ₫
2.471.483 ₫ total
21 Apr - 22 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! (1,000 reviews)
Great place to stay on the shoreline. Privately owned so you.are supporting local businesses!
Reviewed on 10 Apr 2026
The Harbor Front Inn
209 Front St Greenport NY
The price is 4.717.494 ₫ per night from 19 Apr to 20 Apr
4.717.494 ₫
6.142.008 ₫ total
19 Apr - 20 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
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is 4.459.099 ₫ per night from 27 Apr to 28 Apr
4.459.099 ₫
5.753.020 ₫ 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! (261 reviews)
The room was spacious. I’m very clean. I was very impressed. Location easy to get in and out of highly recommend.
Reviewed on 14 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.
