Great Oak Manor

Chestertown, MD Bed and Breakfast

The historic estate on the shores of the Chesapeake Bay.

Great Oak Manor is an exquisite historic estate in Georgian style, located in Rock Hall, Maryland. It’s the perfect destination for a secluded getaway, romantic weekends, and weddings — offering scenic views of the bay, elegant rooms, and an atmosphere of peace and comfort.

1833

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ABOUT US

Your comfort is our priority.

There is a special place just waiting for you on the Chesapeake Bay on Maryland’s Eastern Shore. Our Chestertown, Maryland bed and breakfast is a magnificent country estate built in the Georgian Style. It is a charming B&B with twelve guest rooms and a fabulous family style accommodation in addition to spacious common areas.

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OUR SERVICES

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Whether you want to be active or simply relax, the options are plentiful. Take a bicycle ride on safe country roads, or explore the water from our private beach by kayak, paddle board, or canoe. Walk from our beach to the marina next door where you have access to a swimming pool, a fitness center, and a nine-hole golf course.

To slow down, relax in a hammock shaded by stately old walnut trees, sit by the bay in an Adirondack chair or stroll the expansive lawn. Be sure not to miss our spectacular sunsets!

Room Services

Enjoy the comfort of your room with our convenient in-room dining. From breakfast in bed to late-night snacks, our room service offers a selection of freshly prepared meals and beverages delivered right to your door.

Specials

Our seasonal specials are designed to help you celebrate Maryland’s Eastern Shore in every season! Surprise a loved one with an unexpected getaway in the middle of winter.

Tea & Breakfast

Great Oak Manor provides more than a place to sleep. Located on the Chesapeake Bay in Chestertown, Maryland, we offer a place to dream. Make yourself comfortable as you rest amongst the softest sheets on comfortable beds.

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BEST LUXURY ROOM

Most Popular Rooms

Our waterfront Eastern Shore bed and breakfast has 12 romantic rooms featuring their own unique decor with individual highlights such as a cozy fireplace, a spacious bath with skylight, inviting French doors leading to the garden, or a rich red bathroom. Check out each room for their individual styles and rates.

Deluxe Room

King bed
Private bath
Sunrise and bay views
Electric fireplace
Juliet Balcony

$219/NIGHT

Royal Deluxe Room

King bed
Private bath
Sunrise views
Fireplace
Pet friendly

$269/NIGHT

Luxury Double Room

King bed
Private bath
Bay views
Electric fireplace
Pet friendly

$229/NIGHT

OUR TESTIMONIAL

Our Guest Review's

Great Oak Manor was a true discovery for me! I came alone for a bit of a reset and didn’t expect to find such harmony. A spacious room with a view of the water, quiet evening walks along the shore, a window seat with tea and a good book — everything invited peace and reflection. You don’t feel like you’re at a hotel here, but rather a guest in the home of kind friends. I’m already planning to return in the fall to enjoy the views in a new season.

Robert Fox

GUEST

My husband and I spent a magical weekend at Great Oak Manor! The estate feels like something from a vintage postcard — elegant interiors, antique furniture, a view of the bay, and birdsong in the morning. We especially loved the cozy fireside room and the delicious breakfast served in a bright dining area overlooking the garden. The staff were warm and thoughtful, as if they knew exactly what we needed. It’s the perfect place to escape the hustle and simply enjoy time together.

Jenny Hob

GUEST

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