The Hamptons The Hamptons Travel Guide: Best Hotels, Restaurants & Experiences

A cluster of 17th and 18th-century barns and cottages spread across two acres of manicured lawn, The Roundtree delivers a vacation-home intimacy rare in the Hamptons. Rooms present minimalist contemporary design with Frette linens and Matouk towels behind weathered historic facades. Afternoons bring tea service in the original barn; evenings gather around the firepit for s'mores. Complimentary cruiser bikes make the beach a quick pedal away—ideal for families seeking polish without pretense.

This restored Victorian charmer on Shelter Island channels the glamour of the 1940s, when legends like Sinatra and Monroe reportedly checked in. Views stretch across Long Island Sound from the storied property, while the dining program earns particular praise. Six rooms accommodate families with added day beds, making it a rare find for those seeking old-school elegance without sacrificing practicality.

Greenport's transformation from fishing village to Long Island wine country destination finds its stylish anchor in this 16-room boutique property on Front Street. The monochrome interiors, furnished by Restoration Hardware with hardwood and botanical accents, maintain a refined restraint. A rooftop deck—the town's highest point—surveys the North Fork, while loaner bikes and a Moke electric car encourage vineyard exploration. The ground-floor Bunker Bar provides a convivial base.

Perched above Crescent Beach on Shelter Island, this ninety-year-old retreat spreads across seven and a half acres of Peconic Bay waterfront, its restoration preserving vintage wicker furniture and period signage within contemporary interiors. Sixteen private cottages offer seclusion, while the Terrace restaurant plates farm-to-table seafood from local fishermen. A private charter boat awaits those keen to explore North Fork by water.

Otto Kahn's 1919 mansion—America's second largest private residence—once drew Douglas Fairbanks and Charlie Chaplin to its legendary parties, and later served as the model for Xanadu in Citizen Kane. The estate's theatrical grandeur translates into richly appointed guest rooms with exceptional architectural character. Interconnecting rooms and flexible bedding arrangements make it a surprisingly practical choice for families seeking historic splendor.

Behind Vert Frais's unassuming Long Island City café exterior lies the culinary pedigree of Kanoyama's veteran chef. The shio ramen delivers a fragrant, deeply savory broth crowned with smoky charred cha-shu and crisp bamboo shoots, while sushi-grade salmon scattered over warm rice with glistening ikura offers refined simplicity. The towering soufflé pancakes—impossibly light, barely sweetened—have earned Michelin recognition and devoted followers alike.