Thoughtfully converted from a 19th-century farmhouse and horse barn, this romantic inn sits on 245 bucolic acres in Vermont's Mad River Valley. The property's centerpiece—a Shaker-style round dairy barn built in 1910—is one of only five barns of its kind remaining in the state; beneath this piece of history is a 60-foot lap pool. Innkeepers Ann Marie DeFreest and Tim Piper tend to every detail, from candlelit dinners with ingredients from the inn's certified organic greenhouse-garden to always-stoked fires; there's also an antique pool table, well-stocked library, and plenty of freshly baked cookies for the taking. All 12 comfortable rooms have mountain and meadow views. During winter, guests can ski at nearby Sugarbush Mountain.
Coziest Room to Book: Tucked under wooden eaves, the Richardson Room comes with generous sitting area, whirlpool tub, fireplace, and skylight—you can gaze at the stars from the king-size bed.