Winter Holidays at Maryland’s Small Town and Waterfront Inns

Ever wonder what the holidays are like inside an old-fashioned Christmas card scene? Life appears idyllic and serene. Everyone is happy, the weather is crisp, and time seems to stand still. Experience that tranquility with a trip to a small town or waterfront village in Maryland. 

tilghman-island-hammock-sunset-550x412The town of St. Michaels fooled the British during the War of 1812. There is no fooling around during the town’s 11th annual Midnight Madness celebration, just great deals at shops that are open into the wee hours. Stay at Hambleton Inn or Black Walnut Point Inn to take part in the fun. Continue your tour of Maryland’s Eastern Shore by visiting Brampton Bed and Breakfast in Chestertown or Somerset House in Princess Anne. Venture across the Chesapeake Bay to see boats decorated for the season in Annapolis and make the Charles Inn your home base for a trip to the state’s capital. Continue on your western course to the middle of Civil War country and a relaxing break at Antietam Overlook Farm.
Step into A Christmas Carol at Black Walnut Point Inn. This Tilghman bed and breakfast will be decorated with the 56 Dickens Series. Drive through the bird sanctuary to this waterfront retreat on six acres. Watch the sunrise from the warmth of a private wood cabin or a guest room in the main house. Ask about 20% discounts off weekday two-night stays during December.

hambletoninnRing in the New Year with fireworks at Hambleton Inn. The St. Michaels bed and breakfast is in the harbor and offers a special celebration package. Stay three nights in a water-view room ornamented with seasonal flowers. Toast the getaway with a complimentary bottle of champagne. Savor a five-course dinner and dance the night away at Harbor Lights Restaurant. The package is topped off with a gourmet breakfast for two each morning. 

jr_brampton1Make a New Year’s resolution with champagne and appetizers at the Brampton Inn. Guests are invited to the early evening celebration with views of the scenic Chester River. Take the winter chill out of the air by spending a romantic evening snuggled in front of the working fireplace in your room. Reserve one of the five cottages to start the year off with breakfast in bed. 

Explore Christmas card homes in Princess Anne when you stay at the Somerset House. The December 1 tour includes 38 historic buildings decked out for the season and a reception at the Teackle Mansion. Relive childhood dreams as you watch the holiday parade. Play carols on the hundred-year-old Steinway piano in the living room. Discover antiques and unique collections in every room of this bed and breakfast. 
Feel like you are home for the holidays at the Charles Inn where every window is brightened by a candlelit wreath. Surprise your loved one with a gift under the beautifully adorned tree in the parlor. Hardwood floors, antiques, and original oil paintings add to the old-world charm. Walk through the historic district to the city dock and peek at decorations along the way. 

Santa’s sleigh will easily find you up in the mountains at Antietam Overlook Farm in Keedysville. The entire inn transforms into a Christmas village; you may even glimpse a snowflake or two. Search for Rudolph’s shiny nose in the expansive views of four states and Civil War battlefields. Have visions of sugar-plums as you dream in a queen size bed in one of the five guest suites. 


Other Winter deals: New Orleans Bed and BreakfastsSedona Bed and BreakfastsSanta Fe Bed and Breakfasts