Search results for:

Venture Out Shelter Island provides paddleboard and kayak rentals and guided tours around the island. Perfect for beginners and experienced paddlers alike, the company offers a range of watercraft to explore Shelter Island’s sheltered harbors and scenic coastlines. Read more...

The Shelter Island Country Club is a historic 9-hole golf course dating back over 120 years, offering a relaxed and scenic golfing experience on the island. The course is open to visitors and features beautiful views of the surrounding landscape. The clubhouse restaurant is a local favorite. Read more...

Kayak Shelter Island offers kayak and paddleboard rentals from Crescent Beach, giving visitors a stunning water-level perspective on Shelter Island’s natural beauty. Explore the island’s coastline, tidal creeks, and Mashomack Preserve from the water. Rentals available seasonally with no experience required. Read more...

Dering Harbor Inn is a classic Shelter Island retreat offering comfortable, well-appointed rooms and suites in a tranquil setting overlooking the harbor. Known for its beautiful grounds, welcoming atmosphere, and stunning water views, Dering Harbor Inn has been a favorite among East End travelers for decades. The property features an outdoor pool, spacious rooms, and a location that puts guests Read more...

The Candlelite Inn is a beautifully preserved 190-year-old Victorian inn situated on one and a half acres in the center of Shelter Island. Recently redecorated with care and an eye for period detail, The Candlelite Inn offers five guest rooms with private baths, central air conditioning, and a continental breakfast served each morning. The stunning wraparound porch is perfect for Read more...