TOP 30 Relaxing dining experience in Chestertown, Maryland

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The Driftwood Inn is a charming lodging establishment located at 609 Washington Avenue in the picturesque town of Chestertown, Maryland. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to relax and unwind. With its convenient location near the waterfront and local attractions, the Driftwood Inn is the perfect home base for exploring all that Chestertown has to offer. Whether you're visiting for business or pleasure, the Driftwood Inn provides a convenient and comfortable stay for all travelers.

Play It Again Sam is a cozy cafe and restaurant located at 108 South Cross Street in Chestertown, Maryland. This charming establishment offers a unique dining experience with a menu that features delicious food and beverages. Whether you're looking for a quick bite to eat or a relaxing meal with friends, Play It Again Sam has something for everyone. With its welcoming atmosphere and friendly staff, this cafe is the perfect spot to enjoy a cup of coffee, a tasty meal, or a sweet treat. Visit Play It Again Sam for a memorable dining experience in the heart of Chestertown.

Victory Farm is a charming institution located at 24420 Chestertown Road in Chestertown, Maryland. This unique establishment offers a combination of food and lodging, providing guests with a peaceful and serene retreat in the heart of the countryside. The farm is known for its fresh and delicious farm-to-table meals, made with locally sourced ingredients. Guests can also enjoy comfortable and cozy accommodations, perfect for a relaxing getaway. Whether you're looking to escape the hustle and bustle of city life or simply want to experience the beauty of rural Maryland, Victory Farm is the perfect destination for a memorable stay.

The Shanty Beach Bar is a charming seaside establishment located at 21085 Tolchester Beach Road in Chestertown, Maryland. This cozy bar and restaurant offers a relaxed and laid-back atmosphere, perfect for enjoying a cold drink and delicious food while taking in stunning views of the beach. With a menu featuring fresh seafood, classic bar snacks, and refreshing cocktails, The Shanty Beach Bar is the ideal spot to unwind and soak up the sun. Whether you're looking for a casual meal with friends or a relaxing evening by the water, this beach bar is sure to provide a memorable experience.

Located in Chestertown, Maryland, the Brampton Bed and Breakfast Inn offers comfortable and luxurious accommodations on 35 acres of landscaped gardens, meadows, and forest. With thirteen unique accommodations, including rooms in the manor house and private cottages, each room is carefully appointed with private en-suite bathrooms, luxury linens, smart TVs, and fast wireless internet. Enjoy a romantic retreat with amenities such as wood-burning fireplaces and modern ensuite bathrooms. The historic Brampton Inn, built in 1860 and listed on the National Registry of Historic Places, is a short distance from the quaint town of Chestertown and Washington College. Experience gourmet dining on the beautiful Renaissance Garden terrace or indulge in curated experiences such as a couples' float spa session or a private vineyard tour with wine tasting.