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Step off the fast track to a place and time where the elegant living of yesteryear has been beautifully preserved. At Great Oak Manor in Chestertown, Maryland, the closest highway is the duck flyway and the only traffic you'll see from your charming Georgian-style guestroom are boats sailing on crystal waters. Within this magnificent country estate, recognized by American Historic Inns as among the Top Ten Most Romantic Inns, you'll luxuriate in that "get away from it all" feeling in a private and secluded locale on Chesapeake Bay.
Great Oak Manor
10568 Cliff Rd.
Chestertown, Maryland
21620
Nearest Airport: MTN
We had such a wonderful stay at Great Oak Manor. Every detail was thoughtfully done, from the incredible food and drinks to the warm hospitality that made us feel like family. Cameron and Corine, went above and beyond to make our visit and 20th anniversary so special. We loved the fire pit evenings, exploring the nearby town, touring the property, stargazing, and the breathtaking sunsets. It’s rare to find a place that feels this welcoming and relaxing. We can’t wait to come back again soon!
W88virginia - Fairfax, Virginia
My husband and I had a truly exceptional experience at Great Oak Manor. We can’t recommend this special spot highly enough. The property is beautifully maintained - a mix of antique charm and modern comfort - quiet and picturesque facing westward on the Chesapeake (beautiful sunset views!) We stayed in the Marmaduke room - spacious, well-appointed and comfortable. Truly a retreat - no digital screens or TVs to be found. The grounds include a little beach and fire pit where we enjoyed post-dinner cocktails. The staff made our experience truly special. The property’s new manager, Cameron, was on top of every detail and genuinely cared about ensuring we enjoyed our stay. A trained sommelier, Cameron made fun cocktails (including a lilac aviation made with lilacs harvested in the property) and delicious wine pairings with our fabulous three-course dinner. Do not miss dinner here - the chef prepared an outstanding shrimp and chorizo appetizer, lamb chops, and excellent desserts - all beautifully presented. Breakfast was delicious, as well. As parents of two young kids, we were looking for a place to truly unwind and recharge. We found it here - it far exceeded our expectations. We will be back again this fall.
Flyer29670278274
I searched East Coast weekend getaways and hit a home run. From the minute we pulled up to the front door until we left we experienced the warmest hospitality, delicious food and very comfortable accommodations. The inn, the grounds and the water view are absolutely beautiful! The bald eagle sighting was a treat also. Our room was spotlessly clean and had a fireplace ( the Molton Brown toiletries were a plus too). The town is about 15 minutes away - very cute, safe, clean, walkable, unique shops and a farmer's market on Saturdays. Had a great lunch at Watershed. Special thanks to Werten, Sophia, Cameron, Corinne, Jordan, Dinora and Christy for making our weekend relaxing and enjoyable.
Kara B - Coopersburg, Pennsylvania
My stay at Great Oaks Manor was excellent. It is an intimate gem with impeccable, personalized service and thoughtful design details. And, the food is excellent!
stmccalla - Avondale Estates, Georgia
I have participated in an annual women’s retreat here for the past four years. The moment I walk into the door, I feel at peace and serenity takes over. From the staff who pay such attention to detail and treat you warmly and hospitably, to the welcoming beautiful library, the well-appointed bar, the delicious food, and the comfy beds, the whole experience is simply exquisite. It’s hard to beat such personalized service this day and age. I keep returning year after year, and every year they exceed my expectations!
mwimes - Kansas City, Missouri
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