Book Chestertown Bed & Breakfast

The best time to book a B&B in Chestertown is during the late spring and early summer months, particularly in May and June. This period is especially inviting for travelers who appreciate charming waterfront views and vibrant community events. With comfortable temperatures ranging from the mid-50s to the low 80s Fahrenheit, May and June provide ideal conditions for leisurely strolls along the picturesque streets and enjoying outdoor dining at local cafes.
As the warm weather settles in, Chestertown comes alive with activities such as the annual Chestertown Tea Party Festival in May, which showcases the town's rich history and lively atmosphere. This event draws visitors eager to participate in parades, craft fairs, and live music, all set against the beautiful backdrop of the Chester River.
For those considering a budget-friendly visit, October emerges as an excellent alternative. During this month, the crowds thin out, yet the scenery remains stunning as the fall foliage transforms the landscape into a canvas of vibrant colors. It's a fantastic time to explore the area's historic sites and enjoy the peaceful ambiance without the hustle and bustle of peak tourist activity.