We came with friends who have stayed at the Inn 7 or 8 times. We loved it! The bed was comfortable, the property is just gorgeous and the hosts went above and beyond and met our every need. The home cooked breakfast was amazing, the dogs were great and there were so many places to sit and relax including the swing that I loved. It was a very relaxing weekend and we will return.
Our wedding in September 2016 was absolutely incredible and Great Oak Manor was the star of the show (besides us of course). Spending the weekend and having a place where our family and closest friends could stay with us was invaluable. The house is spectacular and fits perfectly with the beautiful grounds. It was fun deciding which of our relatives and friends would stay in each of Great Oak's large and welcoming rooms. Our ceremony was by the water, complete with bay views and a nice sunset. The back yard was a great setting for our cocktail hour and the side yard was prefect for our seated dinner and dancing. The staff couldn't have been more helpful all throughout the process, and especially during the weekend. A huge thanks to Great Oak and the team for a truly unforgettable wedding for us and all our guests!!
Outstanding in all categories. The breakfasts are a delight, and full of surprises. It is remote enough to be out of the beaten path, but close enough to Chestertown and Rock Hall to enjoy equally outstanding dinners. There is a friendly and helpful staff if you should need anything. The rooms are of equally high standards. It would be difficult to find a better setting, with grounds on the Chesapeake Bay for relaxing and watching the sunsets over the bay. Highly recommended. Gene Larson
My husband and I stayed here for his birthday and it was very relaxing. We stayed in the pond suite and it was gorgeous. The breakfasts were delicious and the grounds were very pretty even though it was the off season. We would love to go back in the summer.
Lovely, charming B&B, right in the heart of Chestertown. Well-appointed, cozy room, comfy bedding, unexpected goodies surprise you everywhere. Cheryl and David are splendid hosts, and Cheryl's home-cooking and baking skills are phenomenal. You will not leave hungry. I look forward to many fabulous future visits!
We could not get hotel accommodations and were concerned about trying a bed and breakfast, but what a delightful surprise! Spotless, comfortable rooms and thoughtful, generous and welcoming host and hostess made this a terrific place to stay. My daughter was playing with National Music Festival and Cheryl invited her to share the delicious, abundant breakfasts with us. Everything was so good, fresh and homemade by Cheryl, who besides being delightful company, is an excellent cook! Her presentation is beautiful as well. David was great with directions, and suggestions of places to see. We had fresh cookies waiting for us when we arrived and were given a generous bag of cookies for ourselves and our daughter for the trip home. They are a great team and do this right!
I had a wonderful time! The dogs were endearing, the complimentary cookies and bottled water were perfect, the onsite library filled with so, so many great books to choose from was the most pleasant surprise! This B&B exceeded even my great expectations. The communal breakfast each morning is delicious and hearty and provides just the right amount of socializing while the sprawl of the place with so many places to sit and meditate provides plenty of opportunity for solitude as well. I loved that the Eastern Neck Wildlife Refuge was just 4.5 miles down the road - I went there two days in a row to explore and sit by the water (best spot is the left turnoff the main road through right before the closing "gate." I thoroughly enjoyed curling up by the pool, on the patio,and in my room, reading multiple fiction books. I also enjoyed sitting out by Rock Hall beach which is just a few miles away from this B&B. Joann and Jim were very hospitable. Also, the cleanliness was great and the bathrooms with the European style tub with a detachable shower head was a treat! Great time and just what I needed. I arrive on. Friday afternoon and left Sunday morning after breakfast.
Everything was great! The staff was very courteous and helpful. All food preparations were unique, well prepared and presented. Love the old charm and country feel. Wonderful weekend getaway, looking forward to our next stay during the week.
What an incredibly restful place, and so close to Washington, D.C. We stayed in the Roese Room, and the pet-friendly policy allowed us to bring Lucy. The staff were great. We are telling all our friends about The Great Oak !
My favorite place in the world to paint and watch birds. Amazing staff, best breakfast I've ever had at a B&B worldwide. Best view. Can't say enough nice things about the character of the building, furniture, library and did I mention VIEW! Eagles, kingfishers, herons, warblers, turkeys, etc. Binoculars provided! Can't say enough nice things about the Inn, Innkeeper, staff, rooms. Favorite place on earth to paint.
MD eastern shore towns can be quite quaint. I wasn't sure what to expect with the B&B. I was pleasantly surprised when we turned the corner and saw a long driveway leading up to a beautiful estate. The innkeepers were more than friendly and took care of our every need. Thank you for a wonderful stay.
A wonderful stay at Great Oak Manor! Beautiful guest rooms, with new comfortable bedding. Lovely new wallpapers and paints. Helpful staff. Tasty breakfasts. Gorgeous sunsets. Great water views. Spacious grounds, terrific for strolling along the shore. Close to historically, architecturally interesting Chestertown. Charming!! Barbara Thompson
This was our 4th visit with Jim and Joanne and they are now almost a part of our family. They are warm and wonderful hosts and make everyone feel like a valued guest in their home. The main house is delightful and the new cottages add privacy and real feeling that you are in your own home on the Bay. They are extremely connected to the local community and can answer any questions. Breakfast especially the bread pudding is not to be missed both for food and table of new friends you will make.
I just returned from a wonderful two stay at the Great Oak Manor Bed and Breakfast. It was so relaxing! The view and sunset was spectacular! The new owners have up dated in and around the Manor. The one improvement was new bedding and linens.The Innkeeper was very friendly and happy to satisfy your every request. She served a fabulous breakfast and dinner. You feel like a special guest. Eileen Kuhn
You know how some really rich people, instead of living in a big house that they have to maintain and keep up, choose to live in a hotel so that everything is constantly being refreshed for them and they don't have to do anything for themselves? This was like the perfect version of that. Great bedrooms, with the comfiest bed I've slept in. The best hosts who made us an endless breakfast. The location was a perfect getaway and/or jumping-off point to explore quaint Chestertown. For what we did (couple's weekend) it could not have been done anywhere better than this.