Great Oak Manor — Hotel in Chestertown

I had the incredible privilege of being the only guest here in this giant, beautiful manor. As Holly and Richard (the spectacular innkeepers) said, I was Lady of the Manor.

I also brought my dog with me. She was even happier than I am, which is saying a lot as she is usually a bit anxious and wary of new situations.

Holly and Richard are so accommodating, so kind, so warm; it's like being home, frankly, which is weird for a manor. That's another thing about this place. It's huge and manor-like but it feels so homey.

I stayed in the Sterling Suite (one of three rooms that accommodate doggos), and it has a door that leads straight from the bedroom outside, which makes doggo potty time super easy. The room is warm and clean and wonderful.

There's a guest pantry and refrigerator, and given the weather, I brought enough provisions for the duration of my three night stay. Breakfast is TO DIE FOR and is included with your stay. Holly is honestly on par with some of the best breakfasts I've ever eaten. She accommodates any and all needs and restrictions (I have none, thankfully) and everything she makes you is perfect. Just perfect. Fresh coffee is available at 7:45 a.m, but there is always coffee and tea available (along with hot chocolate, m&ms, popcorn [there's a microwave]) in the guest pantry 24/7.

Oh, and there's free port and sherry in a globe in the evenings. Because of course there is. This is a manor.

Because I was the only one there I even tried out the piano in the music room. Which is relaxing (if you're not listening to me) and a nice added touch. Feels just like the upright I used to practice on when I was a kid.

The grounds are insane. It's exactly what you'd expect from an English manor replica, with the added bonus of being right on the Chesapeake. And it is quite a bonus. Even in the winter, the beach is stunning, and my dog is just about dead from happiness as she gets to play with the ball in a giant, giant outdoor space (I live in Baltimore).

It was an absolutely magical experience. Thank you Holly and Richard for being just so kind to me and making my trip better than I could have imagined. I could not recommend this place more.

I will be back in the spring/summer with my girlfriends, that's for sure, during which time I will take full advantage of the beach, the kayaks,...

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...

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 a couple 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. 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 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 found GOM- its only an hour away from our home, but feels like worlds away in the very best way. Many thanks to everyone at Great Oak Manor and...