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An elementary school from 1889 until 1939, this building off Main Street was renovated in 1984; today, the limestone shell is the school’s last remnant. The comfy rooms, named after former teachers, are decorated with down duvets on king or queen beds. A hot tub and sauna are on ground level, and guests eat a hearty breakfast buffet in the dining room before heading out on Town Run, a block and a half away. $255-$455; 800-824-1672; washingtonschoolinn.com