TOP 30 Vacation cottage rentals in Chester, Maryland

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The Cottages at Queenstown Harbor is a hidden gem located at 310 Links Lane in Queenstown, Maryland. This lodging institution offers guests a chance to experience captivating sunsets, thriving maritime industry, and endless waterfront views. With a short drive, guests can explore all that the Eastern Shore has to offer, from unique shops and art galleries to visitor-friendly coffee shops and renowned restaurants. Guests can also enjoy premier public golf with two 18-hole courses along 2.5 miles of the Chester River. The professional staff takes pride in providing an upscale golfing experience every day. Guests of the cottages have access to both courses, as well as the sister course, The Golf Club at South River.

Terri Kulp - Coldwell Banker Chesapeake Real Estate is a premier real estate institution located at 114B South Cross Street in Chestertown, Maryland. Specializing in waterfront properties, vacation homes, military relocations, and first-time homebuyers, Terri Kulp offers personalized assistance to help you find your dream home in this charming region along the Chesapeake Bay. With offices strategically located in Easton, Chestertown, and Chesapeake City, Coldwell Banker Chesapeake Real Estate provides unparalleled services to guide you through the process of buying or selling a home in the Eastern Shore of Maryland, Delaware, and Chester County, PA. Whether you are looking to upsize, downsize, or find your waterfront luxury dream home, Terri Kulp and her team are dedicated to helping you make informed decisions on your real estate journey. Contact Coldwell Banker Chesapeake Real Estate today to begin your search for the perfect home in this picturesque part of the country.

Long Beach Marina is a charming waterfront restaurant located at 800 Chester Road in Middle River, Maryland. Situated in a picturesque setting overlooking the marina, this institution offers a delightful dining experience with a menu featuring fresh seafood, grilled dishes, and cocktails. Whether you're looking to enjoy a casual meal with friends or a romantic dinner by the water, Long Beach Marina is the perfect spot to relax and unwind. With its friendly staff, scenic views, and delicious food, this restaurant is a must-visit destination for locals and visitors alike.