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All reviews chesapeake bay private beach view of the bay adirondack chairs breathtaking views get away sterling room my husband and i bald eagles breakfast was delicious eastern shore french toast rock hall could not have been more beautiful property fresh fruit granola
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Reviewed 7 August 2014

I had heard about Great Oak Manor for years, but only recently had the opportunity to plan a trip myself. It was a little difficult to find(could use better signage) but it was well worth the backtracking. The manor itself is a gorgeous movie set like building, and the interior is decorated in an elegant,if faded charming way. However, the true heart of the place has to be the innkeeper Jen. She was a fantastic and warm hostess, and she cooks an amazing breakfast! I hope that this wonderful bed and breakfast will be around for many return visits.

Date of stay: July 2014
  • Trip type: Travelled with friends
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Thank Jennie R
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 23 July 2014

We have returned to Great Oak Manor again and again. It's peaceful, quiet and uplifting. Rooms are well decorated and comfortable. The grounds are fantastic. There's not tons to do in the area so bring your bikes and fishing poles but mostly get ready to relax.

Date of stay: December 2013
  • Trip type: Travelled as a couple
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1  Thank gmogrady
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 20 June 2014

My wife and I spend a lot of our leisure time at B&B's and Inns, especially the Select Registry ones, and we both just loved this place ---- right on the water, beautiful grounds, fabulous common rooms, bald eagles and ospreys all about; just wonderful. The innkeeper, Jen, was just delightful; very warm and engaging, but always with an eye to making sure that we were getting everything that we needed and wanted. We stayed in the Marmaduke Room on the 2nd floor (which I think is one of their larger rooms) which had a wonderful view and the most comfortable bed that I have ever slept in. We will definitely be looking for an excuse to return their soon

Date of stay: June 2014
  • Trip type: Travelled as a couple
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Thank Kevin M
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 16 June 2014

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.

Room tip: Ask for a room with a view of the water. It's also better to get a room on the 2nd floor rather than trudging up to the 3rd.
Date of stay: June 2014
  • Trip type: Travelled as a couple
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Thank billybosso
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 27 May 2014

My wife and I celebrated coming her coming home from Iraq at Great Oak. Immediately, we decided we wanted to have our wedding here. Even 4.5 years later, we are still amazed with the location. Thanks.

Room tip: Room with a view of the water adds to your visit.
Date of stay: December 2013
  • Trip type: Travelled as a couple
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Thank RMELTC
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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