Located along Chesapeake Bay, Wades Point Inn dates back to the 17th century, and it barely survived a British attack during the War of 1812.
The property has four guesthouses, each built in a different era and surrounded by shade trees and twine hammocks. You’ll enjoy breakfast in the Georgian-style main house, built in 1819.
Each room has its own personality—some come with four-poster beds, others are accented with antique rocking chairs and quilted bedspreads. All of the included rooms have views of the bay.
Breakfast typically includes fresh-baked muffins and rolls, fruit, orange juice, and coffee, and it’s served in wicker chairs in the dining room of the main house, which overlooks the bay. The eggs, milk, and meat used for breakfast all come from pastured animals from local farms
You can rent one of the inn’s bikes and explore the coast or hop on a kayak to explore the bay. If you cast a line right from the shore, you might catch rockfish or bluefish.
It’s not unusual to see owls, blue herons, and bald eagles on the property. There’s a list of “must-see birds” on the fridge in the main house.
St. Michaels, Maryland: Seaside Views and Maryland Blue Crabs
Five miles from Wades Point Inn on the Bay, the sleepy town of St. Michaels emanates seaside charm and has a little-known story to tell—its residents outsmarted the British during the War of 1812. The townspeople reportedly hung lanterns in trees outside of town to trick the British into thinking they were dramatically misfiring their cannons. The redcoats overshot and the town survived.
Take a stroll through the area's quaint streets to see its rich maritime culture—you could wile away an afternoon watching ships glide by or trying the area’s famous blue crabs. For a deep look into the town’s history, visit the Chesapeake Bay Maritime Museum or take an educational sailing tour on the HM Krentz skipjack, which departs right from the museum.
What You Get
Stay for two in the Blue, Lookout, Brick, Rose, Daisy, 411, 421, or 426 room with daily breakfast
Option 1: $135 for a one-night stay, valid for check-in Sunday–Thursday (up to a $229 value)
Option 2: $279 for a two-night stay, valid for check-in Friday (up to a $458 value)