The Most Pet-Friendly Hotel

“Experience the beauty of the Eastern Shore with your pet at Great Oak Manor in Chestertown. Pet-friendly amenities include a comfortable pet bed, a warm pet blanket, toys, feeding and water bowls, and treats. The real star, however, is the waterfront setting.”

The Restful Winter Escape You Need

“This country estate provides the ultimate waterfront setting for a relaxing and romantic getaway. You’ll be surrounded in comfort and luxury from the estate’s walled garden to its private beach with a magnificent view of the Chesapeake Bay.”

The Romantic Maryland Getaway

“In need of a romantic getaway? It doesn’t get any more charming than the following bed and breakfast in Maryland. Head here for cozy accommodations, including a fireplace right in your room!”

2020 Tripadvisor Travelers' Choice Award

Based on a full year of consistently receiving great traveler feedback on Tripadvisor, Great Oak Manor was recognized with the 2020 Travelers’ Choice Award. This places Great Oak Manor in the top 10% of hospitality businesses around the globe.

Wedding Wire - 2020 Couples' Choice Award

“The WeddingWire Couples’ Choice Awards® recognize local wedding professionals who demonstrate excellence in quality, service, responsiveness, and professionalism. Winners are determined by the reviews from more than one million WeddingWire couples.”

Gorgeous Styled Shoot at Great Oak Manor

“Two things that will never go out out of style? A perfect lace gown and a grand manor house. Lucky for us, this grand and gorgeous styled shoot has both! The couple was attracted to the venue for the timeless elegance of the architecture along with the flexibility of the space.”