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220 Warrenton St., Rockport, ME 04856, United States

This luxurious coastal resort south of Camden, ME, has had many names, owners, and incarnations since it first debuted in 1889, but that’s only resulted in smart renovations throughout its history. Now it comprises a mix of condo time-shares, private cottages, and 178 guest rooms and suites—each with a balcony or terrace overlooking the ocean. In recent years, the updates continued: the new, zero-entry pool is built into the hillside, with uninterrupted views of Penobscot Bay, and the just-opened Italian restaurant and spa lure prepsters from three new guest cottages. Many of the existing rooms were thoroughly freshened up, and the resort recently committed to staying open year-round. In the winter, expect festive seasonal offerings like an ice-skating rink and a bonfire with s’mores.

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Samoset Resort

This luxurious coastal resort south of Camden, ME, has had many names, owners, and incarnations since it first debuted in 1889, but that’s only resulted in smart renovations throughout its history. Now it comprises a mix of condo time-shares, private cottages, and 178 guest rooms and suites—each with a balcony or terrace overlooking the ocean. In recent years, the updates continued: the new, zero-entry pool is built into the hillside, with uninterrupted views of Penobscot Bay, and the just-opened Italian restaurant and spa lure prepsters from three new guest cottages. Many of the existing rooms were thoroughly freshened up, and the resort recently committed to staying open year-round. In the winter, expect festive seasonal offerings like an ice-skating rink and a bonfire with s’mores.