The three-acre property overlooking Pleasant Bay includes a small beach, a dock for fishing, a fresh- and saltwater pond, and two dining patios. Dating to 1798, A Little Inn on Pleasant Bay was a reputed hiding place for slaves traveling along the Underground Railroad. The rooms are all washed in white and decorated in pastels and bold tartans; 888/332-3351.
Eat: Nearby ABBA restaurant offers a Mediterranean and Thai-inspired menu of fresh seafood and rich desserts. For breakfast, the inn provides a bountiful European buffet overlooking the bay.
Do: Explore local works along the Arts & Artisans Trails and pick up a few gifts or keepsakes for yourself. Or take a short drive to Skaket, Nauset Light, and Chatham Light beaches for a sunset stroll on the beach.