Discover the beauty and fascinating maritime heritage of Maryland’s Eastern Shore as you explore miles of pristine shoreline dotted with charming towns, historic sites, scenic wildlife refuges and breathtaking sunsets across the Chesapeake Bay. Head to the harbor in St. Michaels, the “Heart & Soul of Chesapeake Bay”, for a ride on the historic skipjack or cross the drawbridge to the traditional quaint waterman’s village of Tilghman Island. Immerse yourself in nature at the Blackwater National Refuge in Cambridge, roam the streets of Easton voted the “8th Best Small Town in America”, watch the sailboats passing by in Oxford, one of the oldest towns in America or stroll along the brick sidewalks in the historic college town of Chestertown. Wherever you choose to lay your hat, we have the perfect Eastern Shore vacation home for you to complete your visit.

Eastern Shore Vacation Rentals specializes in marketing and managing short-term vacation rentals – it’s all we do! Vacation rentals are currently the fastest growing segment of the tourism industry and we understand the booking trends! We value both our guests and homeowners and our goal is to maximize your Eastern Shore rental income while offering proactive property care and management to the owner and upscale amenities and top-notch service to our guests. Our state-of-the-art website, unparalleled marketing, and online booking process optimize the booking of your property and our expertise in the vacation rental industry ensures your vacation home is in the best hands. Please contact us, one of our friendly team members is standing by to discuss our Maryland based property management services and how we can best partner with you to grow your investment.