Location and how to get there: Chestertown, Maryland. Situated on 12 peaceful acres, with a commanding view of the Chesapeake Bay, on Maryland’s Eastern Shore, the Inn is 1 ½ hours drive time from Washington, DC, Baltimore, MD and Philadelphia, PA.

Number of rooms: 13 guest rooms all with private bath.

Price range: $155-$285/night, depending on occupancy and time of year.

Time of year to go: Summer, the best prices are available Sunday-Thursday and from January-April.

Located on the banks of the Chester River, Chestertown dates back to 1706, when it served as a thriving mid-Atlantic port of entry for the colonial movement into Maryland. Welcome visitors can follow quaint red-brick sidewalks, along broad shaded streets, as they roam through specialty shops, galleries, antique stores and eateries on their way. On fine summer weekends, evening concerts are often held around the antique fountain in the town square. The secret splendors of Chestertown, however, are the beautiful walled gardens tucked behind the alongside historic homes.

Escape to Great Oak Manor, a quaint Maryland bed and breakfast, where the Chesapeake Bay is aglow in warm sunsets; where towering Oaks gently kiss the skyline and where you can let your body rest and your mind wander. Tucked away on the outskirts of Chestertown, the magnificent 18th century, country-style estate, rests alongside the waterfront. With 11 guestrooms, Great Oak offers the finest in a luxury bed and breakfast inn, where all of your whims are cared for, day and night. Spend an afternoon perusing the quaint streets of historic Chestertown, exploring the Eastern Neck refuge, sampling the fresh catch in Rock Hall, or just curl up in the arms of a weathered Adirondack chair to soak up the view.

Why is your location so great for women?
The Great Oak Manor is a high-end, secluded, waterfront property, close to Washington, DC, Philadelphia and Baltimore. Great Oak Manor is the perfect getaway for a girl’s weekend or a much-needed respite alone.

Services: The Inn is so intimate, that room service is not necessary. Guests feel at home and help themselves to snacks in their room and the Chesapeake Room. A full hot buffet breakfast is available in the dining room, port and snacks available in the afternoon.

Hotel Restaurants & Bars: A personal chef is available to plan a special menu for your getaway. In the conservatory, or outside on the patio, a special wine tasting, or gourmet dinner can be planned.

Health Club: A masseuse can be called for in-room massages, and there is a small indoor heated pool.

Bath products in rooms: Room amenities include luxury terrycloth robes and the finest bath and shower amenities.

Great Oak Manor,
10568 Cliff Road,
Chestertown, MD 21620 USA