Beach vacations in Chestertown, Maryland

Welcome to Jellyfish Joel's Beach Bar, located at 22170 Great Oak Landing Road in Chestertown, Maryland, United States. Our bar is not just a place to grab a drink, but a destination for boaters and beach lovers alike. At Jellyfish Joel's, we take pride in caring for your boat with passion and attention to detail. Our newly renovated on-premise accommodations offer comfortable rooms with amenities such as a mini fridge, private bathroom, and access to ice & coffee stations. Guests can enjoy free parking, free Wi-Fi, and access to the beach, outdoor pool, golf course, and more during their stay. The Lodge is open year-round and conveniently located for local events.

Houston's Dockside Emporium is a charming clothing store located at 315 High Street in the heart of Chestertown, Maryland. Step into this quaint establishment and browse through a curated collection of stylish and trendy clothing items. From casual everyday wear to elegant evening attire, Houston's Dockside Emporium has something for every fashion lover. The friendly staff is always ready to assist you in finding the perfect outfit for any occasion. Come visit Houston's Dockside Emporium and discover your new favorite clothing store in Chestertown.

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.