As local travel experts, we know what travelers are looking for when it comes to finding the perfect accommodations for their next trip. To compile our lists, we scour the internet to find properties with excellent ratings and reviews, desirable amenities, nearby attractions, and that something special that makes a destination worthy of traveling for.

The Eastern Shore of Maryland is arguably the crown jewel of the East Coast. With its coastal charm and breathtaking natural beauty, this portion of the state is a vacationer’s paradise. Luckily, we’ve found just the spot for you to enjoy the best of it all. Great Oak Manor is a waterfront retreat nestled on the shores of the Chesapeake Bay. With gorgeous accommodations and delightful hospitality, this Chestertown, Maryland bed and breakfast has everything you need for a quick getaway.

Ready to book your stay at this gorgeous Eastern Shore bed and breakfast? Click here for reservations and additional information. Great Oak Manor is located at 10568 Cliff Rd, Chestertown, MD 21620. Have you stayed at this lovely retreat before? We’d love to hear all about it!

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