Retro Waterfront Hotel with Luxurious Updates

Forty minutes by train from Manhattan, seagulls call and gentle ocean waves lap at the boat slips along Freeport Creek. The zigzagging roofline of Freeport Inn & Marina has decorated this spot for nearly five decades, ever since the inn made its debut during the 1964 World's Fair. Though it was recently renovated, Freeport Inn retains a dash of '60s swagger thanks to retro touches such as the mod, mid-20th-century furnishings in the front lobby. Sleek and stylish, it's an inviting place to mingle before retiring to the Patio Marina Lounge for waterfront views and fresh seafood.

Deluxe rooms offer a comfortable space to relax. King beds are outfitted with feather comforters, and the showerheads in the bathroom are designed to simulate a hot, heavy rain. At the creek-side Patio Marina Lounge, you'll find cocktails and artistically presented small plates of baked clams ($12) and crispy oyster tacos ($14). A 3,000-square-foot outdoor area dotted with fire pits adjoins an indoor restaurant with a 30-foot bar and high-backed orange leather stools. Mirrored columns in the bar—another retro touch—allow recently restored walls to admire their new coats of paint.

Freeport, New York: Seaside Charm Close to Manhattan

Just a few steps from the inn, Freeport's Nautical Mile invites leisurely, sea-scented walks along a mile of waterfront bordered by bars, restaurants, and shops. New York City is just a train ride away on the Long Island Rail Road, which stops at Manhattan's Pennsylvania Station near Times Square and Broadway. On Long Island's northern shore, the nature trails at Sands Point Preserve wind past christmas ferns, bluebirds, and reclusive rabbits operating secret stills to produce the island's famous iced tea.

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