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November 11, 2012

Great Oak Manor

Great Oak Manor is located on the Eastern Shore of Maryland on the outskirts of historic Chestertown, approximately 90 minutes from Philadelphia and Baltimore. It's a Georgian-style house which has been open as a B&B since the late ‘40s and has 12 rooms. Each is decorated in a period theme, dressed with Williamsburg paint colors, replica antiques, and private baths. We had the pleasure of staying in the Sterling room.

Great Oak Manor's house consists of many shared locations such as the sun room, the conservatory which has a small pool, the library with fireplace, kitchenette  area with TV as well as a DVD/video library (where snacks are left out every night for guests to enjoy), and the music room complete with piano and spirits on the house. I really enjoyed that there were so many spaces we could spend time in and really enjoy the house as a whole instead of being confined to our rooms or being forced off site for a change of scenery (not that you need one). We spent an evening reading books by the fireplace, and our dog, Millie, was right by our side; She seemed to enjoy the fire too.

In addition to the many "great" rooms our private bedroom had a separate sitting and sleeping area, which I appreciated. I'm not a fan of the one large room concept, as it's hard for one person to watch TV while someone else wishes to sleep, so that was well thought out. The rooms had wifi internet and cable, so even while escaping the every day stresses of email and TV, it was nice to be able to check in on occasion.


Every morning breakfast was served and guests had their pick of several options. First there was a buffet table which consisted of fresh fruits, warm baked goods, cereals, yogurt and more, and secondly they offer their guests their choice of freshly prepared dishes. One morning we had our choice of eggs any way we wanted them, choice of toast/english muffin or biscuit and choice of bacon or sausage. I loved that we had choices on top of fresh fruit and cereal, to name a few.  While the food wasn't fancy, it was prepared to your preference.

The B&B is located steps away from the bay, with many activities available on site (some for extra fees) - swimming, boating, golfing, biking, massages, reading, lap pool, exploring the grounds and more.

This B&B is pet-friendly, and the rooms come equipped with a towel and sheet for your pup so that the room and the dog stay clean, and our room had outside access so we could take her outside from our room without bothering any guests. Also, she was allowed in most parts of the house, so she joined us while we relaxed in the library, which was nice, and she got to make some new human and dog friends.

We couldn't control the temperature within our room so it could be very hot or very cold, depending on your preference.

Another thing to consider is that it's far from  "activity" with the closest town of Chestertown being approximately a 20 minute drive, and only a small smattering of restaurants closer than that, so if you're used to being at shops or restaurants within a few minutes, this is not available here. Despite this we still had a chance to visit the local farmer's market and found a book fair in town, so while it's a small drive to get into town, events are taking place most weekends.

Overall Rating:

The staff was very friendly and helpful, and our dog especially loved getting some playtime with Jenn's dogs, so that made it a great experience for her. The property was beautiful and you can tell a lot of time and attention goes into caring for the grounds/building as well as their guests. I would give it a 4 stars out of five.

For more information, or to book your stay, please visit:  


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