TOP 30 Beach retreat in Chestertown, Maryland

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Cliff Point Retreat is a luxurious getaway nestled in the serene surroundings of Chestertown, Maryland. As a real estate and travel agency, we specialize in providing our clients with the ultimate vacation experience. Our stunning property at 4670 Cliffs City Road offers breathtaking views of the cliffs and the city, creating the perfect backdrop for a relaxing and rejuvenating escape. Whether you're looking to invest in a new property or searching for the perfect vacation rental, Cliff Point Retreat has everything you need to make your dreams a reality. Come visit us and experience the beauty and tranquility of Cliff Point Retreat.

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.