Our Vacation Specials & Weekend Getaways

Great Oak Manor on the Chesapeake Bay is the perfect destination for a last-minute vacation or romantic getaway. Located near historic Chestertown, Maryland, we are less than two hours from Washington, DC, Baltimore, MD, and Philadelphia, PA, making our bed and breakfast a convenient spot for your next escape.

Our seasonal specials are designed to help you get the most out of your visit to Maryland’s Eastern Shore, no matter what time of year it is. Surprise a loved one with an unexpected getaway in the middle of winter. Celebrate spring’s return with a much-deserved weekend on the Bay. Discover a multitude of delights while hiking and biking the shore in the summer, or explore country roads amidst the changing colors of fall.