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.
Things to do
Long Island Wine and Food Day Trip with Sommelier host from NYC
฿5,189
per adult
Half-Day Private Long Island Wine Tour Experience
฿9,434
per adult
Private Guided Wine Country Bike Tour in Mattituck
฿6,495
per adult
Top hotels in The Heights
The Chequit
23 Grand Ave, Shelter Island Heights, NY
Stay at this 3-star hotel in Shelter Island Heights. Enjoy free Wi-Fi, free parking and premium bedding. Popular attractions Shelter Island Country Club and ...
8.6/10 Excellent! (29 reviews)
"Excellent"
Reviewed on 10 Nov 2024
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
The price is ฿2,815 per night from 6 Jul to 7 Jul
฿2,815
฿3,237 total
6 Jul - 7 Jul
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. ...
7.6/10 Good! (985 reviews)
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Reviewed on 3 Jul 2025
Baron's Cove
31 West Water Street, Sag Harbor, NY
The price is ฿14,203 per night from 16 Jul to 17 Jul
฿14,203
฿17,850 total
16 Jul - 17 Jul
includes taxes & fees
Stay at this 4-star hotel in Sag Harbor. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
9/10 Wonderful! (258 reviews)
"Really beautiful and clean property that is very convenient and great amenities."
Reviewed on 27 Jun 2025
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is ฿11,373 per night from 31 Jul to 1 Aug
฿11,373
฿13,726 total
31 Jul - 1 Aug
includes taxes & fees
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
9.4/10 Exceptional! (1,000 reviews)
"Loved the service and the relaxing and beautiful resort with history!"
Reviewed on 2 Jul 2025
Sound View Greenport
58775 County Rd 48, Greenport, NY
The price is ฿13,957 per night from 20 Jul to 21 Jul
฿13,957
฿17,609 total
20 Jul - 21 Jul
includes taxes & fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
8.4/10 Very Good! (532 reviews)
"We had an overall great stay and will be back. Especially loved nights out on the beach!"
Reviewed on 22 Jun 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
The price is ฿3,575 per night from 14 Jul to 15 Jul
฿3,575
฿4,111 total
14 Jul - 15 Jul
includes taxes & fees
Stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7.6/10 Good! (1,000 reviews)
"Great location and pool, close to a wonderful restaurant"
Reviewed on 30 Jun 2025
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.
Other neighbourhoods around The Heights
Hay Beach
When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.