TOP 10 Best Waterfront dining in Chestertown, Maryland

Chestertown Cove Apartments is a luxurious residential community located at 408 Morgnec Road in Chestertown, Maryland. Our apartments offer modern amenities and spacious floor plans, perfect for those seeking a comfortable and convenient living experience. Residents can enjoy beautiful views of the cove and easy access to nearby shopping, dining, and entertainment options. With a friendly and professional management team on-site, Chestertown Cove Apartments is the ideal place to call home in the charming town of Chestertown.

Chestertown Landing Apartments is a waterfront community situated at 100 Schooner Way in Chestertown, Maryland. Our luxurious apartments offer stunning views of the Chester River and are conveniently located near shopping, dining, and entertainment options. Residents can enjoy a variety of amenities including a swimming pool, fitness center, and community clubhouse. With spacious floor plans, modern finishes, and a prime location, Chestertown Landing Apartments provides the perfect blend of comfort and convenience for residents looking for upscale living in a picturesque setting.

Chestertown Landing II is a premier waterfront apartment complex located at 200 Clipper Way in Chestertown, Maryland, United States. Nestled along the scenic Chester River, this community offers luxurious living with stunning views and convenient access to outdoor recreation. Residents can enjoy spacious and modern apartments, top-notch amenities such as a fitness center, swimming pool, and clubhouse, as well as a prime location near shopping, dining, and entertainment options. Experience waterfront living at its finest at Chestertown Landing II.

The Waterfront at Washington College is a prestigious university located in Chestertown, Maryland, United States. Situated at 445 South Cross Street, this institution offers a picturesque and serene campus environment right on the waterfront. Students can enjoy stunning views of the water while pursuing their academic and extracurricular endeavors. With a strong emphasis on academic excellence and a vibrant campus community, The Waterfront at Washington College provides students with a comprehensive and enriching educational experience.

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.

Channel Restaurant is a charming dining establishment located at 21085 Tolchester Beach Road in Chestertown, Maryland. Known for its delectable food and inviting atmosphere, this restaurant offers a wide range of dishes to satisfy any palate. Whether you're in the mood for seafood, steak, or a hearty sandwich, Channel Restaurant has something for everyone. With friendly service and a picturesque waterfront location, it's the perfect spot for a casual meal or special occasion. Come dine with us and experience the delicious flavors of Maryland at Channel Restaurant.

Shore Crabbing is a charming seafood restaurant located in Chestertown, Maryland, United States. Specializing in freshly caught crabs from the nearby shores, this institution offers a unique dining experience for seafood lovers. Enjoy delicious crab dishes prepared with local ingredients and served in a cozy waterfront setting. Whether you're looking for a casual meal with friends or a special dinner with loved ones, Shore Crabbing is the perfect spot to satisfy your seafood cravings. Come and taste the flavors of the Chesapeake Bay at this must-visit restaurant.

Tolchester Marina Inc is a charming waterfront establishment located at 21085 Tolchester Beach Road in Chestertown, Maryland. This institution offers a unique combination of a bar, food, and restaurant services, making it the perfect destination for locals and visitors alike. With picturesque views of the water, guests can enjoy delicious meals, refreshing drinks, and a relaxing atmosphere. Whether you're looking to grab a quick bite, enjoy a leisurely meal, or unwind with a drink by the water, Tolchester Marina Inc has something for everyone.

Chester River Yacht & Country Club is a prestigious institution located at 7738 Quaker Neck Road in Chestertown, Maryland, United States. This exclusive club offers a luxurious and picturesque setting for members to enjoy a wide range of amenities and activities. From sailing on the beautiful Chester River to playing a round of golf on the pristine course, members can indulge in a variety of leisure pursuits. The club also features exquisite dining options, a state-of-the-art fitness center, and social events throughout the year. With its stunning waterfront location and top-notch facilities, Chester River Yacht & Country Club provides a sophisticated and welcoming atmosphere for those seeking a premier country club experience.

Welcome to the historic Chestertown bed and breakfast, the Inn at Mitchell House. Rated among the top ten out of 10,000 by "America's Historic Inns," this charming 18th-century manor home is situated on 12 manicured acres between Chestertown and Rock Hall, Maryland. Just a half mile away from the Chesapeake Bay, guests can enjoy the private beach and full services of the Tolchester Marina. Operating year-round, seven days a week, the inn offers six guestrooms, two parlors, a dining room, a screened porch, and numerous fireplaces creating a casual and friendly atmosphere. All rooms and the cottage include modern amenities such as a TV, hairdryer, iron, wireless internet, and use of the 2nd-floor refrigerator. Rates include a full country breakfast for two guests per room.

The White Swan Tavern is a charming historic inn located at 231 High Street in Chestertown, Maryland. This cozy lodging establishment offers a unique and memorable stay for guests visiting the United States. With its quaint atmosphere and convenient location, the White Swan Tavern provides a comfortable and welcoming experience for travelers looking to explore the beautiful town of Chestertown. Whether you are visiting for business or pleasure, the White Swan Tavern is the perfect place to relax and unwind during your stay in Maryland.