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Amagansett is a comfortable spot, almost in the middle of the region between Southampton to the west and Montauk to the east. The Roundtree, part of the Small Luxury Hotels collection, is a fully restored boutique hotel that’s open year-round. Both family-friendly and pet-friendly, the homestead-like retreat has 14 accommodations, divided up among cottages, barn rooms and suites in the main house as well as a meticulously-decorated beach house that used to be owned by playwright Neil Simon.
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