Shelter Island Heights
Travel Guide
Visit Shelter Island Heights
Where to stay in Shelter Island Heights
The Heights
If you're spending some time in The Heights, Sunset Beach and Shelter Island Country Club are top sights worth seeing.
The Pridwin Hotel
81 Shore Road Shelter Island Heights NY
The price is CA $679 per night from Jun 3 to Jun 4
CA $679
CA $853 total
Jun 3 - Jun 4
includes taxes & fees
Book a stay at this beach hotel in Shelter Island Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.6/10 Exceptional! (85 reviews)
"Beautiful, calm and serene. What a nostalgic experience. We’re going back next weekend. A perfect weekend getaway from manhattan"
Reviewed on May 12, 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
The price is CA $121 per night from Jun 7 to Jun 8
CA $121
CA $139 total
Jun 7 - Jun 8
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,003 reviews)
"We used the place as a crash pad - easy to get to from the marina and close to "the main strip" . We did not have a car and it was a holiday weekend."
Reviewed on May 28, 2026
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
The price is CA $1,036 per night from Jun 14 to Jun 15
CA $1,036
CA $1,420 total
Jun 14 - Jun 15
includes taxes & fees
Book a stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Popular attractions Hither Woods Preserve and Hither ...
8.4/10 Very Good! (787 reviews)
"major construction would be ongoing for three of our four days at the hotel. Had we been informed beforehand, we would have made different arrangements entirely. The first room we were assigned had multiple issues: The AC was not functioning, and the room was 80 degrees upon arrival. The “ocean view” ..."
Reviewed on May 28, 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.
Montauk Manor
236 Edgemere St. Montauk NY
Stay at this aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
9.2/10 Wonderful! (1,355 reviews)
"It was a comfortable and welcoming historic property with pretty grounds and a lovely view."
Reviewed on May 29, 2026
Cliffside Resort Condominiums
61475 Route 48 (North Road) Greenport NY
Book a stay at this beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...
9/10 Wonderful! (253 reviews)
"Beautiful property- we would definitely stay there again"
Reviewed on May 23, 2026
North Fork Resort
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
9.2/10 Wonderful! (19 reviews)
"Clean rooms. On the smaller side, so one full room barely comfortably seats 4 ppl. the pool was nice. the staff was very nice. comes with an outdoor seating area and a grill and a fire pit."
Reviewed on May 26, 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.
Popular places to visit
Sunset Beach
Why not spend a carefree afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
Crescent Beach
Why not spend a carefree afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
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.
