We had lived in Maryland for a long time but had never been to Chestertown, just on the other side of the Chesapeake Bay and north from the Bay Bridge. Our children gave us a gift certificate to Great Oak Manor Inn for our anniversary last year, and we finally got a chance to use it. Great Oak Manor is 4-5 miles outside of Chestertown proper, right on the shores of the bay. Driving up to it on the country (dirt) road, the "manor" in the name becomes obvious. With a packed, small-stone circular driveway in the front, the building could be the setting for a story from the early 20th century that we often see on PBS. There have been additions to the building to reach the total of 14 private rooms, but they are on the right side (behind a wall around the courtyard) and not in the main view of the manor.
While we were there for three days, to our disappointment, it rained for the first two. That did not prevent us from seeing the huge lawn overlooking the bay. There are numerous lawn chairs placed closer to the water where good weather would be a magnet for plopping down, camera at the ready, to watch what we heard are some of the most gorgeous sunsets anywhere. On our final day there, the weather was good enough for us to get a closer look at that area and to get closer to the water.
The innkeeper and her daughter were as nice as could be. The daughter took us on an inside tour of the manor as soon as we arrived. The innkeeper herself was a model of efficiency and friendliness, and seemed to be everywhere (but unobtrusively so) at the same time. As for the breakfasts, they were outstanding and creative. They will leave you finding it very easy to skip lunch and spend the day visiting many historic spots in the area, and then have a later dinner at one of the numerous restaurants in nearby Chestertown and Rock Hall.
We will look forward to returning for another visit when the weather is more accommodating.
- Official Description (provided by the hotel):
- Great Oak Manor is located on Maryland's Eastern Shore, where the Chesapeake Bay is aglow in vibrant, warm sunsets; where towering oaks gently kiss the skyline; and where you can let your body rest and your mind wander. Tucked away on the outskirts of Chestertown, Maryland, our magnificent 18th century country-style estate rests alongside the Chesapeake Bay waterfront. With 12 guestrooms and various common rooms, Great Oak Manor offers the finest in a romantic luxury bed and breakfast inn, where all of your whims are cared for, day and night. Whether you're adventurous, need to get away, or just want to be taken care of, there's something here for everyone. Spend an afternoon perusing the quaint streets of historic Chestertown, exploring the Eastern Neck Refuge, sampling the fresh catch in Rock Hall, or just curl up in the arms of a weathered Adirondack chair to soak up the view. Aside from offering a relaxing getaway for travelers, Great Oak Manor also serves as the ideal location for various events, retreats, parties, and weddings. Welcome to our home, stay a while. ... more less
- Reservation Options:
- TripAdvisor is proud to partner with Ebookers, Expedia, Booking.com, Traveltool, S.L.U., Hotels.com and Odigeo so you can book your Great Oak Manor reservations with confidence. We help millions of travellers each month to find the perfect hotel for both holiday and business trips, always with the best discounts and special offers.
- Also Known As:
- Great Oak Manor Hotel Chestertown