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.

Welcome to Great Oak Manor bed and breakfast, a stunning country manor located in the heart of Maryland's pristine Eastern Shore.

The 12,000 square foot mansion was built in 1938 as a private estate. The manor house has been beautifully restored with period decor and replica antiques.

Step inside your room and you'll find a light-filled space with beautiful views and everything you'll need for the perfect stay.

Guests can choose from thirteen unique rooms, each offering their own appeal. Some amenities include views of the Chesapeake Bay, a private soaking tub, fireplace, and king bed.

Each morning, you'll wake up to a gourmet breakfast prepared with fresh and local ingredients. Can you think of a more perfect way to start a full day of vacationing?

The best part about your stay at Great Oak is the surrounding beauty. Whether you're looking for a relaxing ambiance or outdoor adventure, you'll find that the Bay provides the perfect setting.

Experience the water from a sailboat, kayak, or charter cruise as you watch the sun disappear below the horizon.

Or simply relax on the front porch and enjoy the endless water views from the manor house. The inn offers amenities such as kayaks, canoes, paddle boards and a waterside fire pit so you can make the most of the water.

During warmer months, you can enjoy a guided tour of Crow Vineyard & Winery or another nearby vineyard. Great Oak Manor is conveniently situated right along the Chesapeake Wine Trail.

Returning to the inn, you can enjoy a range of spa services or a "Soup-er Supper" in the winter consisting of a homemade soup or chili, cornbread muffins, dessert, and a glass of wine.

So whether you're charmed by this history of the property or the close proximity to the Bay, you'll find your stay at Great Oak Manor to be positively unforgettable.

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!