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Institute of Hotel Management and Catering Technology, Pune

Anyone who’s spent time in Bangkok knows the hotel scene is fairly one-note: Think predictably slick, luxury chain high-rises with expansive city views and, in true Bangkok fashion, swinging rooftop bars. And while we’re all for outdoor drinking just a short elevator ride from our room, we often crave a more intimate, culturally specific stay. Thankfully, private homes are being reborn as boutique hotels (where suites range from around $750 to under $100 a night).

The trend, while slow to emerge, isn’t exactly new—the pioneer was Chakrabongse Villas, the former estate of Prince Chakrabongse before his granddaughter, Narisa, opened it to overnighters in 1998, connecting the two homes and pool by teak footbridges and tiled pathways. (Book the River View suite for a patio facing the Wat Arun temple.) But there are exceptional newcomers like the 1940s AriyasomVilla, which has a gorgeous courtyard and pool, and 24 rooms, some with four-poster beds and Oriental rugs. The more glammed-up Art Deco–inspired Siam Hotel features Connie’s Cottage, a century-old former home that was floated on a barge from the historic capital of Ayutthaya to Bangkok. If you want peace and quiet (not easy to come by in this city), opt for Siamotif, a waterside bungalow that looks out at the red-and-yellow longtails gliding on the Noi canal. Trust us when we say you won’t miss the rooftop bar.

Indecisive travelers, take note: 'Sister properties,' hotels and resorts in different zip codes that share the same owners, are now offering the best of multiple worlds to their guests—two destinations, one trip. Just in time for Memorial Day Weekend, here are four hotel pairings around the country that help you maximize your getaway (because those vacation days are far too precious to spend in one spot).

The Hamptons icon Gurney's recently opened a second outpost in Newport, Rhode Island. It will look familiar: An outdoor pool (the only one at a Newport hotel) is bedecked with the brand’s signature daybeds; Italian eatery Scarpetta draws the well-heeled and hungry. But here, you can take a yoga class on the deck, sip cocktails poolside at The Pineapple Club, and stroll Newport’s downtown cobblestone streets. Plus, the original, Gurney's Montauk Resort & Seawater Spa with its seawater pool, in-the-sand daybeds adorned in yellow and cream, and rosé on Scarpetta Beach, are just a 90-minute boat ride or 15-minute seaplane away.

New Englanders tend to pick sides: the Vineyard or Nantucket. But thanks to Mark and Gwenn Snider—owners of both The Nantucket Hotel & Resort, set in Nantucket’s downtown (often lined by antique vehicles bearing its name); and the Winnetu Oceanside Resort, a sprawling seaside estate on Martha’s Vineyard’s South Beach—travelers don’t have to. Start the weekend celebrating Nantucket’s annual Figawi Regatta and end it water taxiing from the Winnetu into Edgartown for ice cream.

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