Great Oak Manor

Dear Cassandra and John, The Great Oak certainly reflects the love and care you have given it over the years. We wanted a comforting, relaxing retreat from the hectic craziness of our daughters wedding. We were blessed with much more. Thank you for the warm welcome, the friendly banter, scrumptious breakfasts and a taste of home away from home. We wish you all the best. Thank you again for a lovely getaway.

We had been guests at Great Oak Manor a few times when we decided to get married in the beautiful inn. Our family joined us for the weekend. Our ceremony took place in the library and then we all enjoyed a wonderful catered dinner in the Conservatory. We returned recently to celebrate our 5th anniversary and enjoyed a beautiful sunset and a bottle of champagne by the Chesapeake. The innkeepers are the best! They take such great care of their guests - we really feel like a part of the Great Oak "family". Many thanks for providing some of my best memories! If you are looking for romance ... head to Chestertown!

Our third visit; and second in six months! Beautiful, friendly, peaceful, relaxing. Top quality EVERYTHING! John & Cassandra make their guests feel like family.

My husband and I stayed for our five year anniversary. It was better than our honeymoon! The food was outstanding. The room was perfect. The hosts, John and Cassandra, felt like old friends. We loved relaxing in the library in front of the fireplace at night with our port and sherry. It was outstanding. We look forward to returning.

We had a great stay at Great Oak Manor..the setting, the room, the ambiance, the hosts, the food, the dog!

Great Oak Manor Inn was one of the most romantic, most beautiful and inviting inn ever. The host, John & Cassandra were very warm. The fireplace of our room added to the ambience. Riding up to the grand manor and walking in the front door makes one gasp at its beauty. The food was absolutely delicious - the Valentines Dinner was wonderful, the desserts to die for. Breakfast was amazing, there was so much food! The french toast was truly the best I have ever had and elegantly presented. Snacks, fruit, sherry, gourmet cheese & crackers were offered everyday as well as cookies and sodas. John & Cassandra know how to make this one of the best couple of days of your life.

We stayed at the Great Oak Manor last year for our anniversary. Loved it! Great food including a special wine-pairing dinner and very romantic.

We are from Colorado but family lives in the Baltimore area so we were married at the Milton Inn in Baltimore. We wanted a place to go just for one night and found the Great Oak Manor on the internet. This was March so there weren't many people staying but we were treated with great warmth. We sat in front of the fire in our room and in the library and enjoyed the quiet, together. When you finally find your soulmate there is no more romantic place to start a life together than Great Oak Manor. We have been back for 2 anniversaries.

We were engaged, married and celebrated our one year anniversary at the Great Oak Manor! Now our friends and family are fans of this magnificent manor as well. Dana & Brian

My dream place for a romantic getaway. Each room is elegant and comfortable. The solarium is a wonderful surprise for a B&B. The Various sitting rooms were available for casual relaxation or reading. The View from the outside sitting area was amazing especially in the evening when the sunset was at its best. A boater's delight with the adjoining marina.

The most wonderful inn! Gorgeous rooms, fabulous breakfasts and amazing lawn. The Inn Keepers make you feel right at home.

My husband and I have stayed at Great Oak Manor many times, in each of the seasons. It is a magical get-away with the utmost consideration for your comfort. Meals have been delicous, sophisticated and bountiful. We cannot wait to return.

As a last minute decision, I decided to take my husband away for the night. It was a long weekend so I took advantage of the reduced Sunday rate. My husband is a history buff so I looked for a place with a story. I found it and more at the Great Oak Mannor Inn. Even though it was cold outside, inside there were fireplaces (including our room), port and Innkeepers that truly cared about our comfort. And the food, John made the most delicious crab cakes for dinner and breakfast was made to order...yum! The view is amazing, the food wonderful.

Great Oak Manor Inn was the perfect setting to relax in after the whirlwind that is a wedding. With beautiful views of the bay, rustic decor, and excellent service this was the perfect end to a crazy weekend.

The charming setting, professional service and personal warmth we experienced at Great Oak will long be a pleasant memory. Thanks for everything!