My wife and I can't say enough great things about the innkeepers Cassandra and John, and their staff. We would run out of superlatives. They all contributed to making my birthday celebration a memorable one. If you get a chance, visit them once, and you will be hooked for life. More

I recently went to the Great Oak Manor for a "Mommy's weekend off" sponsored by my husband. We had been there together numerous times, but this time it was just me. I loved it, of course! My room was perfect... saw the eagle in the yard! Cassandra was warm and welcoming and confirmed for me, once again, that she runs... More

Our dental group met here for 4 days. It was great in every way. The rooms were very comfortable and the prepared meals were the best I have experienced anywhere. Cassandra and John Fedas understand hospitality. Your need, expressed, is their next goal for accomplishing it. The entire time you feel extraordinary comfort. Cassandra accomplishes this with complete grace. She... More

We spent a lovely weekend at Great Oak Manor. The house sits on a bluff overlooking the bay and facing roughly west so the sunsets are beautiful. Most bedrooms face the water. The main floor has a series of livingrooms - 3 counting the music room, as well as a small garden room and a large reception hall between the... More

We only stayed at the Inn for one night, but it was a great evening! John and Cassandra were great hosts and the INN is a very lovely setting. More

I spent a weekend in this magnificent historic B&B with my friends on a yoga retreat.The place has the best food and rooms are out of this world.I fell like a princess in a castle,rich and pampered and did not feel like leaving.The grounds are inviting for walks or just relaxing by the bay,watch the amazing sunsets or bold eagle... More

I was present for a Yoga Retreat. The wholesome and lovingly prepared meals were extraordinary. The grounds were beautiful and inviting, and the private beach was an added perk! Peace, at its zenith! We had free time to wonder into town, but there was no reason to leave what felt so incredibly comfortable, yet peacefully invigorating! John and Cassandra were... More

This B&B has it all - beautiful rooms throughout, breathtaking views, and amazing food. The innkeepers, Cassandra and John are so gracious and made us feel so welcome. We enjoyed the beach and walking the grounds. It was totally relaxing. We are already looking forward to our next stay. Catherine C. Chevy Chase, MD More

This is a beautiful property with a great lawn that sweeps down to the bay. There is even a small beach for a swim in the bay on a hot summer day. Breakfasts are excellent as well with lots of variety - fruit, yogurt, muffins, something hot each day like french toast or omlettes. The center of Chestertown itself is... More