The best thing about the Great Oak Manor is the view. It really is amazing and the property is huge. There are chairs to sit on, it did get a bit buggy so we couldn't sit out for long. They do provide bug spray which is nice.
The property itself is historic. The addition of the pool looked nice although we did not go in. They provide towels and shower shoes if you want to go in the Bay.
Housekeeping was great, our room was spotless. The towels in the bathroom were very nice.
Breakfast was sufficient. Fruit, cereal, yogurt, muffins and one other thing, one day it was a quiche, the other french toast. What was provided wasn't a lot but what they had was very good. They will make eggs to order but you have to ask for them.
We ran each morning on the road by the Inn. Traffic on it wasn't too bad and we saw a lot of deer.
There were a few downsides of the inn. There is no beach. There is a tiny strip of sand that is probably 4 feet wide by 10 feet long. You couldn't sit out there or enjoy it. When we walked down there were two random people drinking beer there. Part of the reason we booked the Great Oak was for the beach and were quite disappointed when we realized there was not one.
Another downside is that the Manor is right next to a yacht club that is open late with music. The music started around 7 or so and went until at least 1. You could not sit outside in the evening and enjoy the quiet because the music was quite loud. We could hear it in our room as well, but it wasn't loud enough to keep us awake.
While our bedroom was spacious, our mattress was terrible. We probably sunk a good 6 inches when we sat down. It was difficult to get up or move around on it. It really, really needs to be replaced. We stayed in the Marmaduke room.
I say this not being a huge B&B person, but I thought that the Inn was a bit outdated. The fake flowers everywhere were tired looking, the wallpaper in our bedroom was peeling, all the magazines were well over a year old, overall, the Inn was a bit tired looking.
Chestertown did not have much to see or do downtown. I would not go expecting you are going to spend a lot of time there. Our best part of the trip was taking a sail boat ride with Blue Crab Charters in Rock Hall. For $30 a person you get an hour and a half ride on the Bay. It was beautiful. It was by far the highlight of our trip. Rock Hall has a little more to see than Chesapeake, but not much. We went to the 'beach' there which was fine, saved by a great breeze.
I would probably not go back to Great Oak Manor Inn. While the view is indeed great, the price was very high and I do not think it was quite worth it.
- Official Description (provided by the hotel):
- Great Oak Manor on the eastern shore of the Chesapeake Bay is aglow in 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 waterfront. With 11 guestrooms, Great Oak offers the finest in a romantic luxury bed and breakfast inn. ... more less
- Also Known As:
- Great Oak Manor Hotel Chestertown