Great Oak Manor

We planned a long weekend for our anniversary and were excited about staying here. We arrived and were attacked by horse flies that I thought were bees. We literally spent almost no time on the grounds because we were constantly dodging the largest flies It is not their fault, but you should know. The worst part of our stay involves an incident with our car. The parking area was dark and inadequate for the number of cars. We were forced to park in the grass in front of those concrete blocks you see in parking lots. However, what we did not know and could not see due to absolutely no lighting, was that there were pieces of metal rebar holding them into the ground (these concrete bars had sunk into the grass) that were sticking up 6″ from the concrete. We apparently pulled forward enough that the bar caught the underside of our front bumper and did over $ 2000 worth of damage which they refused to cover in any way. To make it worse, the attitude of the inn keepers was rude and they refused to provide the name of the owners so that we could contact them. They insisted that we go through our insurance (not theirs) and we received absolutely no compensation or apologies.
The room was spacious, but the bed was terrible, they need to replace the mattresses. The food was not good, but worse than that they ran out of it every morning. It is a large B&B with many guests and we saw folks being told there was no food left (vs asking them to wait while they prepared more). They clearly need more appropriate well lit parking and I suggest they repair or modify the current parking area.
Better yet, I suggest you skip this place and try somewhere else!

My aunt recently got married here in September and had the manor rented out for the weekend. It was an incredible weekend! The rooms were beautiful and well furnished, the atmosphere was so warm and welcoming. There was breakfast each morning from 8 – 10 and each morning it was delicious! The staff was very nice and welcoming. There is no cell service here, which is actually quite nice because you have to force yourself to disconnect from the world. The mansion is just absolutely beautiful and is set on a bluff that overlooks the water.
It was an absolutely beautiful weekend and it was so wonderful that it went by too quickly. I fell in love with the place and I plan on going back there on my own.

The Great Oak Manor is in the middle of nowhere with no cell service and is honestly a bit creepy when you pull up but it couldn’t be further from creepy. The land is beautiful and I wish I could’ve stayed for a week just lounging in the chairs by the bay and laying on the private beach. The property view of the bay faces west so the sunset was gorgeous and because it is in the middle of nowhere this is a good place to lounge outside and reconnect with a friend, loved one, or even yourself.
The inn keepers are very nice and give a tour of the home and property upon arrival and there is port always available, free soda, and snacks and cheese every after noon (there were peach bars when we got there which were very good).
The rooms are nice and could be a little updated but the amenities provided in the room (free Perrier and still water and biscotti) are a nice touch.
The indoor pool and sun room is a great place for wine before you go to dinner.
RIght next to the Manor is a Marina that is very loud at night (the bar plays music until about 12 AM on weekends) but I couldn’t hear it from my room. The bar looked fun (a little rough) but I didn’t go in.
The breakfast was very good and simple but it is better than having a botched crazy dish. There were fresh homemade muffins that were amazing and the coffee was very good.
The innkeeper told us that a famous family rents out the inn every year for their family reunion and can understand why; what an amazing place to go with a large group to enjoy the huge and beautiful property.
I highly recommend the Great Oak Manor. Only a few small additions would have made it 5 star (turn-​down service, a night cap) but that is just me getting greedy :)

Traditional Eastern Shore luxury in a flawless setting. Planning to be a regular there with my wife. The combination of sprawling Chesapeake Bay view (with bay views in many of the rooms), with excellent continental and trad. American breakfast included, would be enough to draw any seasoned traveler to the Great Oak Manor.
Another major plus is the array of lounge rooms around the ground floor level of this spawling former private mansion. Each room has comfortable seating, cushy sofas and classic old-​style chairs (I’m not much good at identifying style/​eras in furniture so, let’s just say, everything looks warm and inviting).
You’ll also find a bar with choices of wine and soft drinks + evening snacks made up of fine cheeses and fruits, compiementary. Wine is available at an additional cost. The small yet clean and inviting indoor pool awaits you during the sweltering summer season (they may keep it open year-​round, not sure).
The Great Oak Manor Inn is clean, efficiently run, and warmly hosted by its accomodating and friendly hosts (not phony, as I’ve experienced in a handful of B&B’s and Inns), John and Cassandra Fedas.
The nearby towns of Chestertown, Rock Hall, and others are filled with plenty of opportunities for excellent local fare (crab cakes, anybody?) and water sport activities such as boating, fishing, kayaking, etc. This rustic setting and peaceful surrounding farm fields, with plenty of fresh local produce available, may be just what the doctor ordered – it definitely was for my wite and I.