Boutique Hotel Nestled Along a Tributary of Chesapeake Bay

Upon entering the Inn, a cluster of wooden oars poke out of a wooden barrel, as if stowed by a fisherman after a day on the Chesapeake. Across the hall, two pieces of driftwood have been repurposed as lamps, bookending a large painting of a weathered rowboat set in a gilded frame. The Chesapeake Inn's nautically themed interior is a reflection of its stunning, coastal Virginia surroundings.

Thirteen unique rooms populate the inn, each sporting its own coastal décor. Bright walls and maritime accents, including framed maps and tiny sailboats, enhance the seaside feel. A welcome basket of cookies and coffee awaits lodgers in their room, where a king-size bed or two queen-size beds face a 32-inch LCD TV.

White wicker furniture dot the outdoor courtyard, overlooking a tiny pond adorned with wildlife sculptures. The front desk staff rents pedal surrey bicycles at no charge, granting out-of-towners a convenient way to see downtown Urbanna and the Rappahannock River area without strapping a webcam to a seagull.

Urbanna, Virginia: Tranquil Coastal Town Rife with History

Urbanna was founded in 1680 as a port town nestled along the Rappahannock River, a tributary that feeds into the Chesapeake Bay. According to legend, Patrick Henry once addressed the townspeople from the steps of a pub on Prince George Street. The tiny waterfront community packs a lot into a 0.5-square-mile package, with a bevy of restaurants, a historical district, and events such as the annual Virginia's Oyster Festival.

About an hour's drive away, Jamestown Settlement recreates the historic colony, replete with a living-history museum, costumed characters, and gallery exhibits. Patrons can board replicas of the three ships that crossed the Atlantic in 1607, explore the recreated James fort, and learn about Pocahontas's high school crush in a simulated Powhatan village. Relics of the real site can be explored at nearby historic Jamestown, which features excavated ruins of the actual colonial site.