Vintage Mansion in Historic Riverside Village

Like a true country home, Chesapeake Bay's Sandaway Waterfront Lodging bed and breakfast seems to hark back to an idyllic, more laid-back era. Screened porches and old-fashioned rocking chairs overlook the Bay, as well as the Tred Avon and Choptank Rivers. During warmer days before the sea nettles arrive, onsite kayak rentals are available to explore the nearby coves. A perfect afternoon here involves kicking back underneath the mimosa trees on the lawn. Located in one of Maryland’s oldest towns, Sandaway Waterfront Lodging echoes its roots as a Victorian mansion built in 1875 with handsome clawfoot bathtubs and chandeliers.

Rooms spread throughout the mansion’s three floors, where the Old World country aesthetic is shown through antique four-poster beds and plush armchairs. The Carriage rooms are part of the property’s original estate, where horse-drawn carriages would park for the night before the invention of horse-drawn jetpacks. Now the rooms come with bay-facing love seats and wall sconces. Similar decorated deluxe waterfront king and porch rooms include a personal sitting area and private porch, and the various suites have added touches such as canopy beds and bathtubs with room for two. For added privacy, request the Tuckaway Cottage suite that sits just off the main house.

Oxford, MD: Historic Port Town with Sailing and Seafood on Chesapeake Bay

On Maryland’s eastern shore, the village of Oxford maintains its historic charm as a former colonial port for British trade. Locals still enjoy exploring the bay by sailboats, and fishermen unload their catch—from soft-shell crab to striped bass—before hauling it off to local seafood eateries. The surrounding Talbot County encompasses more than 600 miles of shoreline, earning the area the title of “the Hamptons of the Chesapeake Bay.”

Riding a car ferry from Oxford to the nearby towns is a popular way to travel, as the ferry sometimes provides glimpses of mallard ducks, osprey, and other local wildlife. As one of the closest towns to the ferry landing, St. Michaels has several boutiques and restaurants as well as the Chesapeake Bay Maritime Museum, which delves into boat building and the area’s seafaring history.

Read the Fine Print for important info on travel dates and other restrictions.