We had an absolutely lovely anniversary weekend at Great Oak Manor! The service and hospitality were warm and attentive, the attention to detail could not be more spot on. Food was fantastic throughout, so good that we ended up eating dinner there both nights. Fantastic experience- won't be our last visit! read more

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My friends and I had the honor of being invited to a small dinner party hosted by the owner. From the moment we stepped foot onto the immaculate grounds to the end of a beautiful dinner, I was pleased and enamored! The staff was always available and helpful. I can't begin to express how beautiful and luxurious the home and grounds were. The attention to detail in the furnishings and surroundings gave the whole space a simple elegance. Watching the sunset on the Chesapeake was breathtaking. Our host regaled us with the history of the quaint town of Chestertown and of Great Oak Manor itself. Dinner and service were impeccable, as was the conversation! I am appreciative and grateful for the invitation. My friends and I had a once-in-a-lifetime memory and will be back to create many more! Ebony read more

Great Oak Manor - Breathtaking! - Hotels Near Me - Chestertown, Maryland

The overwhelming number of 5-star reviews (645 as of June, 2025) in Trip Advisor incredibly high rating of Great Oak Manor, the amazing service and the feel you get from the photos online are all validated from the moment you arrive to the end of your stay at the Great Oak Manor. The few disparaging comments about management in Yelp's 4 star rating are from 2020 and 2021 and clearly out of date under new management. We had a "hiccup" during our stay that was no one's fault, but the response of the staff was incredibly gracious and accommodating. The Manor house, the rooms, the setting right on the Chesapeake Bay, the attentiveness of the staff are simply the best. My wife and I celebrated our 60th anniversary with and it was like a 2nd honeymoon. This is an idyllic getaway where the hectic pace of life across the bay just seemed to melt away. P.S. Yelp mistakenly describes us as from San Francisco. We are from Columbia, MD, less than 90 minutes away. read more

GREAT OAK MANOR...A MAGNIFICENT WEEKDAY RETREAT We are discerning international travelers with a penchant for a certain mix of understated luxury, authenticity, beauteous settings, environmental sensitivity, locally produced food, and friendly staff. Great Oak Manor exceeds expectations on all counts! This mid-week perfect precious gem getaway destination, would be understated by any written description, and simply must be experienced. We stayed in the exquisite fully kitchen equipped 2 story carriage house, and were graciously shown this boutique hotel's other spacious well-appointed accommodations (for future visits, family gatherings, and executive retreat research purposes). The private beach, and expansive views and stunning sunsets overlooking the Chesapeake Bay were irresistible and indelible. Imagine the view from an endless lawn that seemingly meets the sea much like an infinity swimming pool appears to lead into the ocean. The scrumptious breakfast and carefully curated Michelin star quality meals added to our remarkable guest experience. We seriously hesitated from broadly sharing this review, because we feared GOM would become a favored destination of many who 'might crowd us out' of this superb mid-week heaven on earth haven. But we decided our better unselfish instincts should prevail, so that others might enjoy and commune at this sparkling memory-filled rare gem on Maryland's eastern shore read more

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From the moment we walked into the establishment, we were generously greeted, given the history and a mini tour. We were told that they were making some changes, however from what we experienced the ambiance was impeccable, from the views, serenity, aroma, culture, food...you won't be disappointed!! I am definitely coming back again... read more

Great Oak Manor - Hotels Near Me - Chestertown, Maryland

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Charming and romantic getaway. Great views. Water front property. Delicious breakfast and fantastic innkeepers. Peaceful and quiet.. Will definitely return. read more

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It's a 5 star location for sure but in my opinion the breakfast food that was served was at best Luke warm! And my second day the breakfast was not good at all too but I didn't want to complain because Lamond was so gracious and sweet and helpful it wasn't worth telling her! I know she's a very hard worker and is constantly running around and doing everything I really didn't see anyone doing much except her! There was another guy name Joe he said a few words on our second night at our 5 coarse dinner I did give him a $20 tip to give to Lamond and he said ok I will give to the girls I was thinking what girls! Only person I seen doing anything was Lamond not sure she got the tip but I know tips and fees were included but I felt she definitely deserved more we also had a girl serving wine both nights she was very helpful too both nites her name was Sam she was from Crow Vineyard we tipped her too! She did give us some extra wine that she said would be thrown out but at the end of visit we had wine tab of $50 lol but every thing was good all in all room was nice and clean and the hot coffee every morning was delicious and loved those cookies I think I was only one eating them! Lol I gained 3 pounds after that getaway lol our room was up on 3rd floor and had a cute indoor balcony with a full window across which you could open with screens cause to me room was hot after taking baths! I wasn't impressed with the robes were extremely heavy like they were weighted! And more for a man I put on and had to take off they looked old too! Lol but it was a girls weekend we had fun we go with the flow had lots of laughs and we would go back but definitely need a bigger room but that room was adorable but wouldn't stay in it longer then 2 nites! It was the Geddes room it had great view and we loved the balcony we had drinks up there both days before coming down appetizers and samples of more wine the second nite they had the best salsa I have ever tasted I would of loved to have a gallon of that to go! Delicious! Soups were very hot and delicious too very good cream of crab! Glad they were hot it was only breakfast food that to me were not hot but we ate it! Lol only thing at breakfast that was not good tasting was the Ham very fatty and hard to chew we took home to give to neighbors dog! He liked it! Lol anyway want to personally thank Lamond for everything she even brought my friend a new pillow and gave us more Kleenex when I ask her! She definitely hard worker you don't see that much anymore in these times! Would go back just not sure when at this time! read more

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The Great Oak Manor is in the middle of nowhere with no cell service and is honestly a bit creepy when you pull up but it couldn't be further from creepy. The land is beautiful and I wish I could've stayed for a week just lounging in the chairs by the bay and laying on the private beach. The property view of the bay faces west so the sunset was gorgeous and because it is in the middle of nowhere this is a good place to lounge outside and reconnect with a friend, loved one, or even yourself. The inn keepers are very nice and give a tour of the home and property upon arrival and there is port always available, free soda, and snacks and cheese every after noon (there were peach bars when we got there which were very good). The rooms are nice and could be a little updated but the amenities provided in the room (free Perrier and still water and biscotti) are a nice touch. The indoor pool and sun room is a great place for wine before you go to dinner. RIght next to the Manor is a Marina that is very loud at night (the bar plays music until about 12 AM on weekends) but I couldn't hear it from my room. The bar looked fun (a little rough) but I didn't go in. The breakfast was very good and simple but it is better than having a botched crazy dish. There were fresh homemade muffins that were amazing and the coffee was very good. The innkeeper told us that a famous family rents out the inn every year for their family reunion and can understand why; what an amazing place to go with a large group to enjoy the huge and beautiful property. I highly recommend the Great Oak Manor. Only a few small additions would have made it 5 star (turn-down service, a night cap) but that is just me getting greedy :) read more

Great Oak Manor - Back of House - Hotels Near Me - Chestertown, Maryland

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My new husband and I first fell in love with this picturesque, hidden gem when we toured as a potential wedding venue in Oct. 2019. We were not only memorized by the beauty of the property and the sense of calmness and serenity we felt while visiting, but we were so at ease and impressed with the hospitality when speaking with the main Inn Keeper, Holly about the possibility of hosting our 2020 nuptials there. We had been to several nice waterfront properties up and down the Eastern Shore before we went to Great Oak, but none held a candle to GOM and all it had to offer. Driving into the gates and up the gravel drive, we knew we'd eventually marry at the Manor, and so we signed a contract that day and never looked back. Fast forward 1 year and few wedding bands later, we know without a shadow of a doubt that Great Oak was the perfect home away from home to host our closest friends and family for what has now become the best day of our lives to date. Every time we have stayed at the Manor, both before and after the wedding, the staff has rolled out the red carpet and made us feel so special. And I personally have no words for how enchanting our actual wedding day was from start to finish, how exceptional the whole wedding weekend was - from welcome bonfires to waterfront yoga to relax - words alone are not adequate. We've been told by guests that our event felt like "a summertime lawn party you only see in the movies." But more importantly, Holly, Joe, Lizzie and the rest of the GOM bunch now feel like family to us. Its only been a week since our wedding and I am sad its over/ready to get married there all over again! The good news is we know that Great Oak Manor will hold a special place in our hearts and for our new family for years to come. We can hardly wait to go back for anniversaries and special events, and maybe one day bring our own little ones to visit the Manor and meet the very special people there. We're so glad we discovered this special place- its only an hour away from our home, but feels like worlds away in the very best sense of the meaning. Many thanks to everyone at Great Oak Manor and until next time! As an aside, my husband and I are both attorneys and we were obviously forced to navigate several substantial contracts in the midst of uncertainty caused by a global pandemic. I just wanted to note how refreshing it was to deal with an extremely reasonable vendor like GOM during 2020. We never once were concerned or felt uncomfortable with the contractual obligations of either party and GOM was always transparent and open to discuss any legal or contingency aspects we felt were ripe for discussion. read more

Great Oak Manor - Hotels Near Me - Chestertown, Maryland

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We purchased a two night mid-week stay in the Russel Suite. Due to the pandemic, we could not stay as originally intended. When we were finally able to use our purchase, Great Oak charged us $220 instead of the original $170 we were expecting. The Innkeeper, Holly, had a chance to advise me of this price change when we spoke on the phone, but chose not to and waited until our arrival to make a cash grab. They also offered a 15% discount, but the guest had to ask for it, and then only the room charges were discounted, not the associated taxes. These events indicate corrupt business practices and left a lingering bad taste. The rooms were way overpriced, even when discounted. Physically, the facility has seen better days. The beds were luxurious, but the antique furnishings were shopworn and many in need of repair. The location, billed as relaxing, was simply remote. With only breakfast provided, guests are obliged to drive 16 miles round trip to the nearest town twice a day for meals. Speaking of which, the restaurant selection in Chestertown is pedestrian at best, and many close early and on Mondays. If you choose to go, keep your expectations low and you won't be disappointed. read more

Fabulous hosts. Wonderful location. Amazing charm. You will love this place as much as we do!

Wonderful, romantic getaway! We were looking for a place that was nice but not crowded. This place was perfect! Very hospitable staff; warm and friendly but left us alone when we wanted it. The room (D'Oench) was wonderful. Breakfast outside was just lovely. We used the kayaks and bikes for short outings. Enjoyed visiting Chestertown during the day, even though not a lot was open because of the pandemic and us going during the week. I'm a runner and really enjoyed running alongside the cornfields on quiet roads. Definitely recommend for those looking for a relaxing time away. read more

My husband and I spent two nights here for our 25th wedding anniversary. I found it by Googling B&Bs in Maryland. It looked great online and was even better in person. Joe, the innkeeper, was friendly and available whenever we needed anything. Our room (the Russell Suite), was comfortable and had a spacious bathroom. The room was clean and well appointed and gave us a much-needed getaway. We enjoyed a bottle of local wine in the solarium overlooking the beautiful grounds. We had hoped to take one of the canoes out, but the water was too choppy. We did make some tea (pantry available 24 hours a day with complimentary coffee, tea, popcorn and snacks) and sat on the beach and watched the birds diving for fish. I initially made our reservation and then saw a 25% off special. I emailed the innkeepers and asked if they would honor that and they agreed and credited our reservation. We are hoping to return with some other couples and make it an "event". Why not? You will not regret your decision to visit. read more

We really enjoyed the grounds the views are spectacular. Holly and Richard did a great job. We will definitely be back this winter. read more

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My husband and I spent two nights at Great Oak Manor for our baby moon. We had such a wonderful time, even better than we imagined. Our room, the Hynson, was clean and comfortable. The bathroom was really nice and also clean. The inn keepers were so friendly and accommodating. They asked us at every opportunity if everything was to our liking and how we were doing. You could tell they really enjoy what they do and really care about the guest experience. We opted to have them cook us a dinner for two on our first night, and Holly called us that morning to ask what we'd like prepared. Everything was delicious. The breakfasts were also delicious, a couple warm options (delicious pecan french toast and turkey bacon/egg cups the first morning, baked oatmeal with cranberries and croissant sausage bake the second morning), toasts, fruit salad, and granola with yogurt or milk. I have some dietary restrictions and they were extremely accommodating which was greatly appreciated. They also have a guest refrigerator and snack pantry that was available 24/7, stocked with some snacks, coffee, tea, sodas etc. Alcohol available for purchase. We really enjoyed walking around the grounds, which were beautiful even in January. The property backs up to the water which makes for breath taking views. They had the woodburning fireplaces lit in a couple of the common areas on the first floor, and we were able to sit down there and chat and enjoy each other's company in the evenings. The rooms have direct tv with HBO. Overall, this was an excellent experience and we will definitely be back! Highly recommend to anyone considering staying here. read more

We've been to several B&B's and this is our favorite so far. The manor is beautiful and has great vintage touches that make it feel extra homey and historic. The grounds are gorgeous and we never wanted to leave. We spent most of our time outside enjoying the view. It seemed like a lot of people didn't take advantage of the offerings but we sure did. Canoe. Kayak. Hammocks. Cruiser bikes. Breakfast was soo good and the hospitality was perfect. Innkeepers were helpful without being overbearing. We'll be back! read more

As our toddler approaches 2 years old, my wife and I finally got away for some down time and we happened upon Great Oak Manor for our getaway. We absolutely loved it! On our way we stopped into Chestertown to the Hotel Imperial for lunch- we were blown away with incredible fare and terrific service. When we arrived at Great Oak Manor, we got the grand tour before checking in to our room (Marmaduke). The Georgian Manor is truly gorgeous inside and out. We surveyed the vast grounds and a short time later were canoeing on the bay. Our room was spacious and comfortable and breakfast was outstanding! We look forward to returning. read more

Great Oak Manor - My wife getting a detail picture of the woodwork. - Hotels Near Me - Chestertown, Maryland

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My aunt recently got married here in September and had the manor rented out for the weekend. It was an incredible weekend! The rooms were beautiful and well furnished, the atmosphere was so warm and welcoming. There was breakfast each morning from 8-10 and each morning it was delicious! The staff was very nice and welcoming. There is no cell service here, which is actually quite nice because you have to force yourself to disconnect from the world. The mansion is just absolutely beautiful and is set on a bluff that overlooks the water. It was an absolutely beautiful weekend and it was so wonderful that it went by too quickly. I fell in love with the place and I plan on going back there on my own. read more

Traditional Eastern Shore luxury in a flawless setting. Planning to be a regular there with my wife. The combination of sprawling Chesapeake Bay view (with bay views in many of the rooms), with excellent continental and trad. American breakfast included, would be enough to draw any seasoned traveler to the Great Oak Manor. Another major plus is the array of lounge rooms around the ground floor level of this spawling former private mansion. Each room has comfortable seating, cushy sofas and classic old-style chairs (I'm not much good at identifying style/eras in furniture so, let's just say, everything looks warm and inviting). You'll also find a bar with choices of wine and soft drinks + evening snacks made up of fine cheeses and fruits, compiementary. Wine is available at an additional cost. The small yet clean and inviting indoor pool awaits you during the sweltering summer season (they may keep it open year-round, not sure). The Great Oak Manor Inn is clean, efficiently run, and warmly hosted by its accomodating and friendly hosts (not phony, as I've experienced in a handful of B&B's and Inns), John and Cassandra Fedas. The nearby towns of Chestertown, Rock Hall, and others are filled with plenty of opportunities for excellent local fare (crab cakes, anybody?) and water sport activities such as boating, fishing, kayaking, etc. This rustic setting and peaceful surrounding farm fields, with plenty of fresh local produce available, may be just what the doctor ordered--it definitely was for my wite and I. read more

In early July 2020 my fiance and I drove out to the Eastern Shore to tour wedding venues. We saw several but fell in love with Great Oak Manor ("GOM"). The manor and grounds are absolutely beautiful! Also, GOM allows pets and we have two pups that absolutely have to be a part of our special day. I was soooo relieved to have found our venue and we provided GOM with a $500 deposit to reserve our date. Holly, the innkeeper, emailed us the contract about a week or two later. The contract didn't have a force majeure clause (a clause that excuses performance of the contract for both parties if there is a pandemic/act of god/fire, etc.) or a rescheduling provision - so we asked Holly for GOM to supplement the contract with language they had used in the past. She requested that we draft language that we thought was "reasonable," so we did (we are both attorneys). We submitted the draft language to her within a week and waited OVER A MONTH for GOM's attorney to review the language and submit his or her suggested edits. The attorney completely deleted the language we drafted and included a force majeure clause that only benefited GOM (i.e., did not excuse performance for us - the client - if this pandemic is still ongoing) and permitted rescheduling (with a sizeable fee) only if the pandemic is the reason for the rescheduling. Also, GOM even RAISED the prices/fees for several items in the contract and required payment in full (we are talking close to 20k) 9 MONTHS BEFORE THE WEDDING DATE with no chance of a refund FOR ANY REASON WHATSOEVER. We were baffled and totally turned off to say the least. Not to mention, the delay in getting the revised contract caused a great strain on our ability to solidify our plans. When we attempted to further negotiate with GOM in good faith, we were basically told "this is our contract now - take it or leave it." Well, we left it and are now in a terrible position of trying to find a new venue for June 2021. As all of us brides know, planning a wedding is an emotional journey. Unfortunately, GOM's actions (or more like inactions) caused us great anguish and disappointment in what should be a joyous time preparing for our special day. read more

We spent a wonderful weekend at this lovely Bed and Breakfast. If you are looking for a place to relax, this is the spot for you. Holly and Joe were great hosts. Joe seems to know everyone in town and directed us to the local spots where we were treated like family. We will definitely come back to Great Oak Manor. read more

Fabulous location. Owners are great hosts. The one complaint is that the bathroom is tiny with a prefab shower. Everything else was wonderful! read more

Beautiful venue and extremely helpful staff. Missing one star for not being more handicap/wheelchair accessible.

We had a wonderful time at Great Oak Manor. The place is very secluded and the scenery is spectacular. One of the highlights was the ability to watch the sunset over the bay. It was so beautiful that my children put down their cell phones and ran outside to enjoy it. The living area (we were in the large suite) was beautiful, clean and accommodating. Holley and Richard were the perfect hosts. Breakfast was delicious!!!!! We look forward to a return visit. I already miss their hammock where I was able to fully relax, watch the water and enjoy a book. WELL DONE. read more

We only stayed one night but had a lovely stay. The Innkeepers could not have been more welcoming. The grounds are beautiful with amazing views of the bay. After our arrival we sat under the oaks and read. It was so peaceful and quiet until they started mowing the grass. But, I guess that has to be done....so we went inside. Our room was perfect with a comfortable bed and large bathroom. Even with antiques I felt like it was not dated. I do like having a TV and I know some B and Bs don't have that. Our internet worked fine with their wifi. The breakfast the next day was yummy. I looked up the recipes for the bacon wrapped baked eggs and praline french toast so I could make at home for a very special occasion! I'm sure we would have used more of the amenities if we had been there for a longer time. I'd go back again. read more

I recommend this place!!!!!! Food - The breakfast that was provided was DELICIOUS! The egg dish was very tasty and they even had homemade granola for the yogurt. Room - The room I stayed in was called the Hynson. It had high ceilings and a great view of the waterfront. The bed was comfortable and the sheets were clean. I was very impressed with the cleanliness of the bathrooms and the amount of towels that were provided. The Grounds - The Manor is set on the waterfront and provided a beautiful scene. There was a lot of room to walk around and explore. They had a small beachfront that you could walk along and see the bay up close. Down by the water, there was also a place to have a bonfire. I even saw two Bald Eagles land on one of the trees that were on the back of the property. It was amazing because i had never seen an eagle up close before. Inside, they had a lot of space to hang out, enjoy the view and just relax. Overall - This Bed & Breakfast was more than I could have asked for. The Innkeepers were very accommodating and went above and beyond for their guests. This was a great place to unplug for the weekend and enjoy the beauty of the bay. I would recommend this Bed & Breakfast to everyone!!!!! read more

I would not recommend Great Oak Manor. While the grounds were kept up well, the common areas were clean, and the view was tranquil, the owners seemed preoccupied and almost annoyed we were there. They didn't share any suggestions on things to do or places to eat except when we brought up Crow Vineyard which was nice but not if you're vegetarian. We were never asked if we needed anything or how our stay was. The Sterling Room had no drawers and a lot of dead bug marks on the walls. DO NOT GO KAYAKING! The current is very strong and there was never a mention of this. The breakfast was good but one day was very light and we were starving an hour later. DO NOT GET THE SMORES KIT unless you want to stick your hand in the fire to roast the marshmallows. There was a guest fridge which I appreciated but then when we went to get some leftovers a couple hours after we checked out, they had thrown everything out without any warning. When we asked them about it, they said they thought we left but kept the alcohol which they did return to us. This is funny to me for so many reasons: 1. We never felt like they noticed us there the whole time. 2. I didn't use all of the smores kit and they through out half of it. 3. They were going to drink out alcohol : ). The overall stay felt more like a hotel than a B&B. Despite all of the good reviews, I would not recommend. read more

We absolutely love this inn!! We've been returning several times a year, because it's truly the best place to stay if you want to lower your stress level and be pampered. Lamond and Joe are the consummate hosts. They make sure that every need is anticipated and met. There is a calm beauty about Great Oak that is hard to find elsewhere. The house is beautifully decorated and full of light. You can enjoy the library with a seat by the fireplace, or the conservatory with its 270 degree view of the grand back grounds and the water. Every night the sun sets over the water right behind the inn, and it's wonderful to sit on the Adirondack chairs and watch. There is also a beach with kayaking and other fun water activities. They serve a gourmet breakfast, and there is 24 hour coffee, tea, sodas, granola bars and homemade cookies every day. Make your reservation early -- it's getting very popular! read more

This is my new favorite getaway spot-- a historical manor house with clean, quiet rooms, lawn right on the bay and delicious breakfasts. Have your morning coffee on the beach, head into Chestertown for the afternoon and have a sherry or port in the parlor before bed. The hosts are wonderful people with lots of stories to share about the property over the years. We will definitely be staying there again. read more

Very lovely property and the setting is perfect. It was very relaxing to sit and gaze at the bay and to watch the sun set in the evening.The staff was friendly and accommodating and the breakfast service was prompt. Our room (Russel) was spacious and comfortable. While there where numerous positive aspects to our stay, for the price of $329/night, there are certain things one expects and small details matter. When we arrived, there was no staff to be found and we had to walk all around the first floor to find the unmarked reception desk. Over the course of the two day stay, I had to direct several couples who had just arrived to the reception desk because they also couldn't find it. Each couple commented that after a long drive, they didn't want to be searching for the desk or a staff member. We would suggest a small plaque with an arrow. While it was nice to have access to a pantry stocked with beverages and snacks, we didn't care for the fact that chilled bottles of water were in a common guest fridge loaded with guest's food. It seemed a bit "too homey" and we would have preferred to have water available to us in our room. There were no tissues in the room, only one robe, no soap at the sink to wash your hands and the toilet paper was one ply. We were a bit disappointed with the breakfast. One of us had requested scrambled eggs one morning due to dietary restrictions- they had absolutely no flavor and tasted of cooking oil. The next morning we were presented with baked eggs in bacon cups. While the eggs were cooked well and nicely seasoned, the bacon was very undercooked and couldn't be eaten. It would have been nice to have baked goods such as muffins, croissants or bread with our breakfast. We typically try and leave positive reviews but wanted to leave you with some item for your consideration. read more

Walt Okon - Great Oak Manor; 9 June 2016 - More than Excellent, this B&B is Outstanding. Upon arrival we were greeted by the Inn Keepers and immediately given a tour of the house and grounds even before checking-in. We were impressed with how clean everything was and the attention to detail of everything. The Manor has been restored with quality products and quality work; ceiling to floors. This place passed my IG inspection with flying colors. The huge lawn areas on the property were well groomed and real grass cut perfectly with no weeds. How do they do that? Just wonderful. Our room (The Tylden room) on the 2nd floor had a view of the water which was magnificent. The room and private bath were perfectly clean. Absolutely no negatives. I did not expect the internet to be good in such a remote area; but, to my surprise it worked fine in my room and I did not have to go to any of the hot spots in the manor. Breakfast was perfect and served exactly on time at 9 AM. The coffee bar outside of the dining room was ready early and the coffee was great. There was a separate mini kitchen with a serving bar for coffee and afternoon tea with fresh baked cookies. Also, a fine Port was available in the music room. Rosie played the piano in the music room after breakfast. This place is just wonderful. We watched the sun set and walked the beach. Rosie brought home a piece of drift wood. Bottom Line; I checked out the other B&Bs; Great Oak Manor is the best by far. Walt Okon, Springfield, Virginia. Green Features: The heating and Air Conditioning unit is green, so quiet and effective, we did not know it was on until I adjusted the temp. Walt Okon, Springfield Virginia read more

My parents just got back from a two night stay at Great Oak Manor and can't stop raving about it! They say the breakfast was really tasty and they liked the variety, Mike and the staff were wonderful and the location was amazing. They said they had a great view from their room and loved sitting outside and watching the sunset. They also enjoyed the fire their first night. They went on and on about how helpful Mike and everyone was, how they told them interesting facts about the hotel (Marilyn Monroe apparently stayed there- my mother was excited!) and how they made they feel so welcomed. My mom reported that the room was clean and a "good size" and she loved that they provided large amounts of shampoo, conditioner and body wash (and not just little travel sizes). They are also normally very early risers and were so relaxed that they slept in both days. They said they can't wait to go back! Mike & Team- thanks for taking care of my parents and making their short getaway wonderful. They are home safe and are meeting their newest grandbaby (born yesterday) for the very first time! read more

We just returned from a 2 night stay at Great Oak Manor. It is a gem and we cannot praise it enough. If you want to relax and refresh while you sit overlooking the Chesapeake Bay watching beautiful sunset/rises or eagles/osprey soaring above your head then this is the place for you. Easy drive to Chestertown, if you can pull yourself away from the quiet and beautiful setting. Friendly, welcoming, excellent service. read more

Every time I stay here I fall a little more in love! The food is amazing and the staff is so accommodating. I just love waking up and having a cup of tea in the lawn, overlooking the bay before breakfast, that is how I want to start every morning. We ordered crabs and the innkeepers set up tables outside for us with crackers and everything we needed. The water was too rough for me to use their paddle boards but next time I want to explore the area with them, I love that they are included and you don't have to rent anything to keep yourself busy there. read more

This is an update to a negative review that I posted earlier. After my negative reviews, I was contacted by a representative of the Inn's insurance company and encouraged to file with my insurance for damage we sustained to our car on the property. They led me to believe that they wanted to resolve the issue and help us recover for our damages and the only way was to file with my insurance. Well, I did so (which I was not going to do since we did not want a recordable loss) and when my company went after them this 3rd party ruled that the Inn was not liable. All of this, despite the modifications and repairs made to the property, that are clear evidence that they were in the wrong. I cannot support this Inn, its Innkeepers or owners. Stay at your own risk. Of course, since my reviews they have apparently added lighting and fixed the rebar issue, but of course they are not at all at fault right? read more

Lovely place. Stayed here 1 night while dropping of my kid to Echo Hill Camp. Although this place is absolutely gorgeous and the two guys running it were friendly they serve breakfast at 8.30! Absolutely ludicrous and done to suit themselves. A pool was advertised and there wasn't one just the HORRIBLE marina. The late breakfast is why they get 2 stars. read more

Great Oak Manor used to be our favorite bed & breakfast. During our most recent visit, however, the maids forgot to clean our room. In addition. the breakfast was not up to par either. In the past, breakfast was always cook to order, and fresh. The previous Innkeeper, Jen was amazing. During our recent visit, breakfast was buffet style, and not good. Eggs were for breakfast every day we were there (sitting out at the buffet). We honestly could have gotten a better breakfast at Bob Evans. For the price, we were very disappointed. You should invest in a real Innkeeper who has a culinary background. It felt like we stayed at the Best Western. We hope things improve because we used to love this place. read more