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. 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!
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!
Services
The story of the property, where our Chestertown, MD bed and breakfast was later built, begins in 1659 when Josiah Fendall (1628-87), fourth Colonial governor received the land as a gift from Cecil Calvert, Second Lord Baltimore.
The name is believed to refer to a large oak tree that marked one of the corners of the property.
Now offering luxury B&B lodging on the Chesapeake Bay, the 12,000-square-foot manor originally was built in 1938 as a private residence for Russell D'Oench.
Born out of the bricks from the ballast of W.R. Grace sailing ships, Great Oak Manor was styled after an 18th century English country retreat.
The name is believed to refer to a large oak tree that marked one of the corners of the property.
Now offering luxury B&B lodging on the Chesapeake Bay, the 12,000-square-foot manor originally was built in 1938 as a private residence for Russell D'Oench.
Born out of the bricks from the ballast of W.R. Grace sailing ships, Great Oak Manor was styled after an 18th century English country retreat.
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.
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.
Check out each room for their individual styles and rates.
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.
At our Eastern Shore pet-friendly hotel, we understand how difficult it is to leave your furry family members at home or in the kennel.
However, at our Inn, you're fully welcome to bring them along so they can have fun with you!
We want your companion to be as comfortable as you are, so we have designated three rooms at the Inn for you to choose from, all offering accommodations specially catered to our guests with pets.
These rooms are all conveniently located, having either direct or close access to the outdoors, that way you can have an easier time tending to their needs.
However, at our Inn, you're fully welcome to bring them along so they can have fun with you!
We want your companion to be as comfortable as you are, so we have designated three rooms at the Inn for you to choose from, all offering accommodations specially catered to our guests with pets.
These rooms are all conveniently located, having either direct or close access to the outdoors, that way you can have an easier time tending to their needs.
Our Eastern Shore bed and breakfast is the perfect destination for a last-minute vacation or romantic Chesapeake Bay getaway.
Located near historic Chestertown, Maryland, we are less than two hours from Washington, DC, Baltimore, MD, and Philadelphia, PA, making Great Oak Manor a convenient spot for your next escape.
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.
Celebrate spring's return with a much-deserved weekend on the Bay.
Located near historic Chestertown, Maryland, we are less than two hours from Washington, DC, Baltimore, MD, and Philadelphia, PA, making Great Oak Manor a convenient spot for your next escape.
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.
Celebrate spring's return with a much-deserved weekend on the Bay.
Gift Certificates from Great Oak Manor can be purchased in any dollar amount, are treated as cash and expire one year after purchase date.
They can be used for a future stay or on any of our packages or enhancements.
Simply specify the amount of your choosing as you are purchasing online.
Once your Gift Certificate purchase is complete, we will email (or mail) you or the specified gift recipient a PDF of the Gift Certificate.
To book your reservation using your Gift Certificate, simply call (410) 778-5943 with the Gift Certificate code found on the Certificate.
They can be used for a future stay or on any of our packages or enhancements.
Simply specify the amount of your choosing as you are purchasing online.
Once your Gift Certificate purchase is complete, we will email (or mail) you or the specified gift recipient a PDF of the Gift Certificate.
To book your reservation using your Gift Certificate, simply call (410) 778-5943 with the Gift Certificate code found on the Certificate.
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