Georgian House Bed and Breakfast in Annapolis, MD. Photo courtesy of the author.

One of the greatest joys of visiting a new location is to get to know the favorite local spots. Staying at a Bed and Breakfast might be one of the best ways to uncover these local hideaways. These small lodging businesses provide a homey and intimate getaway where guests can wake up to a home-cooked meal, often enjoyed with the owners.

The Bed and Breakfast industry has experienced its fair share of obstacles over the past five years. One of the main obstacles has been the advent of streamlined home-sharing services such as AirBnB. Not to mention, as the Coronavirus swept the nation, many lodging establishments experienced empty homes for the first time. Nonetheless, Annapolis remains home to a handful of Bed and Breakfasts owned by people dedicated to sharing their home in the heart of Maryland's capital.

The Flag House Inn

The Flag House Inn is located on Randall Street, steps away from the main entrance of the Naval Academy. While the building has served as a Bed and Breakfast for over 20 years, the current owners; Carmel and Marty, have operated it for the past two and a half. After moving to Annapolis to run The Flag House Inn, they jumped headfirst into the task of getting to know the area.

The Flag House Inn on Randall Street has been a B&B for over 20 years. Photo courtesy of author.

When Marty considered his favorite restaurant in Annapolis, he laughed off the question with, “That’s like asking me to pick my favorite child!” Though hesitant to choose, he landed on Galway Bay Irish Restaurant, whose staff made him feel welcome when he arrived into town five months ahead of his wife. Another favorite is Boatyard Bar and Grill, where you can find one of the best crab cakes in town at the right price.

The Far East King Suite is one of five artfully decorated rooms at the Flag House Inn, drawing inspiration from paintings. Photo courtesy of the author.

With COVID restrictions limiting some of the more common Annapolis pastimes, they have been focusing on introducing guests to a wider variety of outdoor activities. We asked Carmel what her favorite activity is, and she immediately answered that she loved going out for sailing cruises on the Schooner Woodwind.

The Fleet Suite is another room available at The Flag House Inn. Photo courtesy of the author.

They have also been sending guests to nearby hiking trails and parks such as Beverly Triton Nature Park in Edgewater and Matapeake State Park on Kent Island. These parks offer quiet beaches and winding trails that offer plenty of room for social distancing.

The Inn at Horn Point

Another Bed and Breakfast in the area, The Inn at Horn Point, is tucked away in the streets of Eastport. Owners, Cory and Carol, are no strangers to outdoor recreation in the area. They are avid bikers and enjoy exploring their favorite park in Annapolis, Quiet Waters Park, or their favorite trails on the Eastern Shore.

The colorful sitting room at the Inn at Horn Point. Photo courtesy of the author.

They also enjoy strolling around the area surrounding the Smithsonian Environmental Research Center in Edgewater. The couple's organically grown and hand manicured garden, which encompasses their spacious wrap-around porch, is also a sentiment of their love for the outdoors.

Cory and Carol in front of their B&B, The Inn at Horn Point in Eastport. Photo courtesy of the author.

Cory and Carol often “dine-around,” frequenting spots such as Vin 909 Winecafe, The Point Crab House and Grill in Arnold and Carrol’s Creek Cafe, right on the water in Annapolis. They also enjoy the casual ease of Eastport Kitchen & neighborhood dive bar, Davis’ Pub.

An original clawfoot tub at the Inn at Horn Point. Photo courtesy of the author.

When there were no social distancing restrictions, the couple enjoyed attending theatre and live music in the area. Some of their favorites being a local radio station, 103.1 WRNR’s Private Artist Showcases and shows at The Annapolis Summer Garden Theater and Colonial Players.

The Georgian House

The Georgian House, located on Duke of Gloucester, has long-term ties to the Naval Academy and the Historic District in Annapolis. Ann and Tom have been the owners of the house since 2005 when they relocated to Annapolis during their son’s time as a Midshipman. The house is 260 years old and has hosted 3 of the 4 Maryland signers of the Declaration of Independence.

Garden and Patio of the Georgian House Bed and Breakfast. Photo courtesy of the author.

Ann is a member of the Naval Academy Chapel Guild, where her love of gardening shines while adorning the Chapel with flowers. They also host several Midshipmen every year as a sponsor family- a home away from home.

The Thomas Stone Suite, named for one of Maryland's signers of the Declaration of Independence.

The garden at the Georgian House, where guests often enjoy their morning coffee, has been featured in the Secret Gardens of Annapolis Tour. Ann has curated the garden herself with many trips to Homestead Gardens.


The sitting room at the Georgian House Bed and Breakfast. Photo courtesy of the author.

Ann is very active within Annapolis. She has worked hard to preserve her home's history and character and has been very involved with Historic Annapolis as well as Visit Annapolis over the years. They are active supporters of St. John’s College and send their guests over to attend  free art openings and lectures. She believes that it is crucial to be involved in the city that she represents and has tirelessly endeavored to do just that.

Open Homes, Open Hearts

Annapolis is home to many fabulous restaurants, rich history, beautiful art, interesting people, and so much more. Staying at any one of these Bed and Breakfasts offers a unique lodging experience that guests travel from all over to have. Trust us, simply ask what their favorite local activity is, and you could be discussing options with these knowledgeable owners for a while.

The gated entrance and original sign to the Inn at Horn Point. This house is just one of the many Bed and Breakfast operations in Annapolis. Photo courtesy of the author.

Each of these establishments is the product of the heart and soul of the owners. Their boundless knowledge allows travelers to get to know Annapolis from a unique perspective. With their home open to you, they will open your eyes to the heart of this beautiful town.