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“Amazing mini-moon stay!”
Review of Great Oak Manor

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Great Oak Manor
Ranked #2 of 11 Chestertown B&B and Inns
Certificate of Excellence
GreenLeadersGold level
Reviewed 20 August 2014

My husband and I escaped to Great Oak Manor for a quick three day mini-moon after our wedding. Everything about our stay was perfect! The manor is beautiful, the food is delicious and the hospitality is exceptional! It was the perfect spot to sleep late, read on the grounds all day (and spot bald eagles in the trees just over our heads!) and go for lazy bike rides and walks. We ventured into Chestertown twice and had a great time exploring Washington College and the old homes and history in the town. We were also pleasantly surprised by the variety or dining options - Lemon Leaf Cafe was a particular favorite! I highly recommend Great Oak Manor- it offers the ideal combination of rest and relaxation and activities in a truly stunning setting!

  • Stayed: May 2014, travelled as a couple
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Thank juliamartin1007
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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245 - 251 of 386 reviews

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.

  • Stayed: July 2014, 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.

  • Stayed: December 2013, 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

  • Stayed: June 2014, 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...
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  • Stayed: June 2014, 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.
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  • Stayed: December 2013, 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
Reviewed 25 May 2014

We celebrated a birthday and tea party weekend at the manor. It is a very impressive architectural example in beautiful surroundings with a wonderful view of the bay. We stayed in the Caulk room which was fine but I was mislead by the website describing a private terrace on which you can enjoy a sunset cocktail. It is more of a door that leads to a small porch area with a dirty table and two deck chairs...for the money select another room. We never met the Innkeeper which was disappointing. The breakfast was ok but I thing cherrios and yoplait yogurt really do not belong on the table of a inn such as this. The sherry and port were a nIce touch. The marina next door though really did not help the ambiance...at least on memorial day weekend. Bad garage band music really did not help the experience. Maybe that was just a holiday weekend deal but if that is a turnoff you better check with the marina to get the summer band schedule.Dont get me wrong...we enjoyed our stay. The inn is a bit dated but thats part of the charm. If you want all updated and new a 1938 bed and breakfast is not the way to go. The history of Chestertown and the old beach resorts of Kent County I find fascinating. Chestertown once being the busiest colonial port is a fact many do not realize. Its a nice weekend getaway for history buffs with enough dining and shopping to satisfy those not so locked to history. The tea party is fun even if not proven to be historically accurate...take a walking tour and learn all about that and some very interesting historical facts of the period....we paid 8 dollars for the tour and our guide was very interesting and informative.

  • Stayed: May 2014, travelled as a couple
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Thank traveler594652
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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Additional Information about Great Oak Manor

Address: 10568 Cliff Rd, Chestertown, MD 21620-4115
Phone Number:
Region: United States > Maryland > Chestertown
Amenities:
Bar / Lounge Beach Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Pets Allowed ( Dog / Pet Friendly ) Suites
Hotel Style:
Ranked #2 of 11 B&Bs / Inns in Chestertown
Price Range: £118 - £222 (Based on Average Rates for a Standard Room)
Hotel Class:3.5 star — Great Oak Manor 3.5*
Number of rooms: 13
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 
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Also Known As:
Great Oak Manor Hotel Chestertown

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