ABOUT

An exceptional experience awaits you at Great Oak Manor. Our 1938 Georgian manor looks out over a picturesque Chesapeake Bay near the historic village of Chestertown along Maryland’s Eastern Shore.

Twelve comfortable accommodations and a delicious breakfast will make you feel right at home. Relax in a hammock shaded by stately walnut trees, recalibrate to nature’s pace as you gaze over an ever-changing bay view. Stroll the expansive lawns or ride further afield in one of our Cruiser Bicycles.

As the new owners of Great Oak Manor our journey in hospitality began over 20 years ago. Today, our focus is on placing the Manor on a trajectory to achieve extraordinary service while creating a deeply personalized experience for our guests. At each touchpoint from website, through arrival, and departure and beyond we aim to build loyal guests and strong relationships, not scale.

We want the Manor to be a place where our guests can focus on the things that matter to them in a place of congenial graciousness. For individual travelers, couples, families, and groups of friends we want to become a first-choice option for connection, for learning, and wellness.

We will be very deliberate in leveraging the rich history of the Manor and the surrounding area to help create the powerful shared experiences from which memories are created.

For many years, Great Oak Manor has delivered a rich hospitality-driven experience to its guests. Under the leadership of General Manager, Brooks Bradbury, we have a bedrock commitment to build on this legacy.

MAP

HOURS

ADDRESS

10568 Cliff Rd. Chestertown, MD 21620

PHONE

(410) 778-5943

EMAIL

WEBSITE

https://www.greatoakmanor.com

PLAN YOUR VISIT

FREQUENTLY ASKED QUESTIONS

Curious about frequently asked questions like "Where to park?" and "What time does First Friday start?" Click here to find all the answers you need in our comprehensive FAQ section.

UNLOCK THE CHARM OF CHESTERTOWN

Discover the insider knowledge on where to find the best cream of crab soup in town, indulge in the tastiest ice cream, and plan your visit to the art galleries. Let us guide you to create a spectacular experience in Chestertown that combines culinary delights, sweet treats, and a journey through the town's vibrant art scene.

DOWNLOAD WALKING MAP

Chestertown, Maryland was founded in 1706. It was established as a port town and played a significant role in the colonial era, serving as a bustling trade hub along the Chester River. Today, Chestertown retains much of its historic charm and is known for its well-preserved 18th-century architecture and vibrant cultural scene. Thanks for checking us out!

EMAIL

office@mainstreetchestertown.org

PHONE

(410) 778-2991

OFFICE

Chestertown Town Hall
118 N. Cross Street
Chestertown MD 21620

MAILING ADDRESS

PO Box 427
Chestertown MD 21620

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