Great Oak Manor

One of Maryland's historically significant estates, Great Oak Manor sits on twelve acres directly on the Chesapeake Bay in Maryland's Eastern Shore, eight miles from historic Chestertown. With large common rooms and beautifully appointed... more

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Great Oak Manor

Here is what guests had to say...

"astounding" 11/17/2008
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Stayed On: 11/2008

Such a beautiful place. All care is taken to make each guest feel spoiled. It's my new favorite B&B! read more
"Pamper yourself - Visit Great Oak Manor" 10/2/2008
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Stayed On: 9/2008

Innkeepers John and Cassandra Fedas were so friendly and accommodations and made my visit so relaxing and comfortable. I didn't want for anything. I was able to relax and anjoy some quiet time as well as see the area! My visit was too short!

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"A Fabulous High Life Weekend at the Great Oak Manor" 7/23/2008
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Stayed On: 7/2008

Great Oak Manor is intimate, personal, and high end. If I told Cassandra that I wanted to have dinner at a particular place, she would dissapear and return with dinner reservations. Chestertown itself is a cool little college like town with a lot... read more
"Memorial Day Weekend" 5/29/2008
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Stayed On: 5/2008

The Great Oak Manor is a great place to stay. The manor house is wonderful, with beautiful views and places to relax. The grounds are extensive with many places to take in the views of the Bay. The rooms are very comfortable and the hosts will... read more
"My first time, will not be my last time" 5/26/2008
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Stayed On: 5/2008

Cassandra and John, my friends and I had a wonderful time at Great Oak Manor. We did not what to leave, but in our leaving we are truly inspired to spread the word of how wonderful our experience was at Great Oak Manor! The rooms were spacious and... read more
"Great Oak Manor" 5/15/2008
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Stayed On: 3/2008

The Great Oak Manor provided a great getaway from a very busy life. The innkeepers were a delight. What an enchanting place. We would love to return.

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"What a relaxing retreat!" 4/30/2008
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Stayed On: 4/2008

We've had a wonderful week-long stay at the manor this april 2008. The location is gorgeous and the rooms absolutely lovely. Owners and staff went out of their way to make us feel at home. We highly recommend this B&B and would love to come back!

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"Great Oak Manor" 4/30/2008
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Stayed On: 3/2008

The Great Oak Manor provided a great getaway from a very busy life. The innkeepers were a delight. What an enchanting place. We would love to return.

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"A quiet, secluded retreat" 4/28/2008
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Stayed On: 4/2008

My husband planned a surprise weekend getaway to celebrate my special "milestone" birthday. He selected the Great Oak because it looked to be a wonderful secluded place to relax and get away from the hustle and bustle of our busy lives.... read more
Innkeeper Response
I was happy to read that you found your stay with Great Oak Manor Bed and Breakfast to be “all in all a lovely place”. Therefore it saddened me that I misread you on your arrival. It is our intention for our guests to feel at home. I am very sorry if I made you feel hurried or uncomfortable. Arriving frazzled during the dinner hour, perhaps you misinterpreted my intention in the abbreviated tour. Although most Bed and Breakfast Inns are the innkeepers home, we fully understand that it is a 24/7 responsibility. Dinner for us is usually a juggling act that we try to keep invisible to our guests. My elderly father also lives with us so we try to keep his meal on schedule. I am sorry I did not take the time to fully explain the situation. Most of our good local restaurants have their last seating at 8 PM and I wanted to insure you would get proper seating. Your enjoyment on your days spent here are up most on our minds and I would not have wanted you to spend it at a pizza parlor. I guess I should have taken a few minutes to explain all of this, I am sorry. As for the stemware that was removed from your room, sincerest of apologies are in order. We hope that you recognize that staff inadvertently removed these items not knowing their value to you and significance. They simply assumed that the glasses were ours as it is highly unusual for guests staying with us to bring such valuable and precious items. We do offer Anniversary Champagne on silver trays with champagne flutes. Our morning shift just did not realize they were yours. Our staff also mistook your empty bottles of water for ours since this is also offered complimentary. We have had a talk with all the employees so that they are more aware of personal items that should not be handled. I hope this brief letter helps to explain our actions and in some small measure retrieves the good name of Great Oak Manor Inn. I hope that sometime in the future you will return to a full measure of hospitality.

- Cassandra Fedas (innkeeper)
"Superior ambiance" 1/24/2008
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Stayed On: 12/2007

Restful, welcoming, friendly hosts. 5 star dinner. Elegant and tasteful.

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"Great Oak Manor." 12/12/2007
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Stayed On: 11/2007

Beautiful ocean view b&b on the eastern shore. Great Oak Manor is a beautiful and peaceful b&b. The house is elegant and majestic, and the view is spectacular, over the Chesapeake Bay. The rooms are comfortable and elegant with nice modern... read more
"We'll go again" 10/14/2007
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Stayed On: 10/2007

My wife and I have stayed at B&B's around the world and Great Oak Manor is right there with the best of them. Ask Casandra to help arrange a crab dinner on the back patio. It was great and we will return.

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"Great Place to Relax" 9/13/2007
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Stayed On: 9/2007

Our 4 day stay was absolutely relaxing. Beautiful surroundings, great host and hostess. Beat breakfasts, especially the crab quiche. We didn't want to leave! Helen & Joe read more
"Beautiful and Relaxing" 9/2/2007
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Stayed On: 8/2007

This is the 4th time we stayed at Great Oak Manor and we will keep coming back. The house is gorgeous and every room has its own beauty and charm. The property itself couldn't be better as it faces the Chesapeake Bay as well as Fairlee Creek. What... read more
"Annual Scrapbooking Weekend" 5/16/2007
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Stayed On: 3/2007

I am part of a scrapbooking group consisting of 12 to 16 women who all share the passion of working on our family albums. This past March we celebrated our 10th annual weekend at Great Oak Manor. Each year we all look forward to our weekend away... read more
"Relaxing by the bay" 5/10/2007
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Stayed On: 4/2007

Just like the Otis Redding song "Sitting by the Dock of the Bay, the Great Oak Manor has perfected the art of getting away by the bay. When asked by friends to find something wrong with our three-night stay all we could think of was that it was... read more
Innkeeper Response
Thank you so much for taking the time to write about your experience at Great Oak Manor. We are thrilled you enjoyed your stay and can't thank you enough for the wonderful review.
- Cassandra Fedas (innkeeper)
"A perfect weekend getaway" 2/4/2007
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Stayed On: 2/2007

My wife and I make it a point to go somewhere special on our anniversary every year. We had never been to a B&B before. Cassandra (the owner & innkeeper) was abolutely delightful, and made the weekend very special. We were very pleased... read more

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Contact Information

Great Oak Manor Bed and Breakfast
Great Oak Manor, Chestertown, MD - Inn
Great Oak Manor
10568 Cliff Rd
Chestertown MD 21620-4115
USA
Phone: +1-410-778-5943
Fax: +1-410-810-2517
Toll-free: +1-800-504-3098
Innkeeper(s)
Cassandra Fedas
Rates:
$165 - $310
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Reviews

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Read all 17 Reviews
Review Great Oak Manor, Chestertown, MD

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Great Oak was built at a time when grandeur was more important than cost, when craftsmen were artisans and when houses were built to last for generations to enjoy. The Manor was built in the tradition of the 18th Century with bricks from the ballast of W.R. Grace sailing ships. A relaxing and memorable Bed & Breakfast on Maryland's Eastern Shore.A great getaway. The Chesapeake room is one of six common rooms available to our guest, for evening Port and Sherry, reading one of our 825 books, games, TV or movie watching, or simply relax by a winters fire.
The Conservatory, with west facing glass enclosure you can view the sunsets year round.Sitting with views of the bay, this elegant fireplace dining room features a full breakfast with Manor-baked muffins, hot entree, cereals, yogurts, and always fresh fruit. Welcome!
The Marmaduke Room - named for the first land grantee from Lord Baltimore overlooks the bay and is one of our deluxe waterviews with a king bed, sitting area, private bath and fireplace.D'Oench a deluxe waterfront room with king bed, fireplace expansive water views, sitting area, large private bath, and like all of our rooms equiped with luxury bathrobes hair dryers, irons and ironing boards. Come and relax.
Hodges, with a four posted queen, fireplace and large private bath is a great estate setting at a reasonable price.The Roese suite is two rooms. One with a king bed and writing area with desk. The other is a gracious living room with fireplace, sofa and sitting area with television and lots of light. The cathedral ceiling private bath and walk in closet add to this suites elegance.
The Roese suite is two rooms. One with a king bed and writing area with desk. The other is a gracious living room with fireplace, sofa and sitting area with television and lots of light. The cathedral ceiling private bath and walk in closet add to this suites elegance.