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The cobblestone streets and historic landmarks of idyllic downtown Newport offer photo-ops at every turn. Stay with Inspirato at five-bedroom Odyssey—a quintessential, three-story New England architectural gem. The home’s crown jewel is a furnished rooftop deck looking out over the harbor and bridge. And just outside town lies Spindrift, a bright and airy four-bedroom home right on the water with its own private dock.