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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is £67 per night from 19 May to 20 May
£67
per night
19 May - 20 May
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! (1,008 reviews)
Parking was easy, A/C worked. WiFi was weak in the room. Bed, covers, pillows OK. Good value for the price.
Reviewed on 17 May 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
The price is £145 per night from 21 May to 22 May
£145
per night
21 May - 22 May
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! (499 reviews)
Amazing. Loved everything about this place and will be back. The rooms were surprisingly spacious and the decor was perfect. I wish the pool was opened but I guess only for true summer. A great value and we will be back.
Reviewed on 16 May 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is £340 per night from 31 May to 1 Jun
£340
per night
31 May - 1 Jun
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! (647 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 £270 per night from 31 May to 1 Jun
£270
per night
31 May - 1 Jun
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! (614 reviews)
Nice room and view
Reviewed on 15 May 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is £228 per night from 25 May to 26 May
£228
per night
25 May - 26 May
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)
Bedding was suboptimal and toilets clogged. Additionally, very noisy due to 2 weddings in the resort that night… so not very relaxing.
Reviewed on 17 May 2026
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is £206 per night from 31 May to 1 Jun
£206
per night
31 May - 1 Jun
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! (269 reviews)
Very helpful staff. Room was very roomy (no pun intented) and appeared to be recently upgraded. Chit provided for continental breakfast at a local coffee shop that was very good. Definitely recommend.
Reviewed on 5 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.
