Great Oak Manor
Great Oak Manor is a newly renovated 12-room Georgian-style luxury boutique hotel located on an oasis of stately trees and expansive lawn on Chesapeake Bay a few miles from the quaint village of Chestertown in Kent County on Maryland's Eastern Shore.
Hours
See website for hours.
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March 31, 2026
stmccallaExcellent, welcoming
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!
Read MoreMarch 30, 2026
mwimesA Serene Retreat
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...
Read MoreMarch 14, 2026
Paulette B10/10 Would Highly Recommend
Great Oak Manor is an absolute gem and place I would highly recommend. From the moment you arrive, you’re surrounded by breathtaking views, warm hospitality, and a peaceful atmosphere that instantly...
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