The largest island in the contiguous United States reaches a long arm out into the Atlantic from Brooklyn to Montauk, where the King & Grove hotel group has followed the summer crowds east. Set in a patch of lakeside woodland, Ruschmeyer's resembles a retro summer camp, with ping-pong tables in the beachy Sand Bar, activities from bike-riding to bingo, and live music performances. The restaurant serves fresh Montauk seafood, while DJs entertain in the Electric Eel Disco.
Ruschmeyer's, 161 Second House Road, Montauk (001 631 668 2877; kingandgrove.com). Doubles start at $275 (£183), B&B.
The Inn at Windmill Lane, Amagansett
This peaceful inn is the ultimate high-society hangout. A short walk from Indian Wells Beach on Long Island's South Fork, it offers seven pristine suites with hardwood floors, marble bathrooms and whitewashed walls, plus three private cottages with immaculate interiors and stone patios outside. Linked by lavender-lined pathways, they all come with modern artwork, kitchenettes and snug lounges strewn with chic coffee-table books.
The Inn at Windmill Lane, Amagansett (001 631 267 8500; innatwindmilllane.com). Doubles start at $375 (£250), B&B; cottages from $925 (£617); each sleeps two.
The Maidstone, East Hampton
Swedish hotelier, Jenny Ljungberg, takes historic buildings and gives them a lick of paint. The Maidstone is a fine example. Constructed before the US Civil War, it was used as a tannery and converted into an inn during the Roaring Twenties. Ljungberg bought the property in 2008, adding the Buddha Garden, free yoga classes and cool Kronan bikes. Each of the 19 rooms is themed around a Scandinavian personality, from Karen Blixen to Alfred Nobel.
The Maidstone, 207 Main Street, East Hampton (00 1 631 324 5006; careofhotels.com). Doubles start at $365 (£243), room only.
The Capri, Southampton
The Capri is where the cool crowd flock to. They come to lounge around at the Bathing Club, sink a cocktail under the stars and then tuck into slabs of filet mignon at the BLT Steak restaurant, before heading out into the Long Island night. Mostly though, they come to crash in one of the cool, calm rooms, with vintage artwork curated by fashion designer Cynthia Rowley and toiletries by luxury spa brand June Jacobs.
The Capri, 281 County Road, 39A Route 27, Southampton (001 631 504 6575; caprisouthampton.com). Doubles start at $199 (£133), room only.
Jedediah Hawkins Inn, Jamesport
The North Fork of Long Island has a reputation for good food and fine wine. Set apart from the crowds of the Hamptons, amid fragrant gardens and farmland, the Jedediah Hawkins Inn aptly reflects the area's charms. It has one suite and five guest rooms that range from nautical to homely. But the real draw here is in the free wine tastings at 14 nearby vineyards and the celebrated farm-to-fork restaurant by executive chef Lia Fallon.
Jedediah Hawkins Inn, 400 South Jamesport Avenue, Jamesport (001 631 722 2900; jedediahhawkinsinn.com). Doubles start at $279 (£186), B&B.
Sunset Beach, Shelter Island
Hotelier André Balazs has taken a former motel on the sands of Shelter Island and turned it into a chic beachside retreat. With a portfolio that includes The Standard hotels in Manhattan and the Chateau Marmont in LA, here Balazs has converted 20 suites and added a lively French restaurant that dishes up moules marinières, salade Niçoise and bouillabaisse. Bikes are available to explore dry land, while pedalos and kayaks open up the ocean waves.
Sunset Beach, 35 Shore Road, Shelter Island (001 631 749 2001; sunsetbeachli.com). Double rooms start at $311 (£207), room only.