Washington College graduation

Your New Favorite Place to Stay Near Washington College

Just a few miles down the road from our Eastern Shore inn is one of the most historically significant colleges in the United States. Washington College is named after its most famous philanthropist and board member, George Washington, who actually received an honorary degree after becoming our nation’s first President. It was the first college … Read More

Happy women with yoga mats

Rejuvenating Wellness Retreats at Great Oak Manor

Refresh your mind, body, and soul with some much needed self care and make your health and wellness a priority this year. Whether you are craving some “me time” or want to get away with a few of your very favorite people, find your zen at Great Oak Manor, the ideal destination for reflection and … Read More

Two women shopping in chestertown - walking into a store

Winter Group Retreats

Are you feeling a little frazzled and disconnected from your friends after the craziness of the holidays? Make memories and build bonds to last a lifetime with a group retreat this winter on the Chesapeake Bay. We understand that organizing several people for a single experience can be difficult, but it doesn’t have to be! … Read More

Geese flying in a sunset sky

Your Guide to Hunting on the Eastern Shore

The Chestertown, Maryland area is known as one of the best hunting destinations in the east. With a long-standing tradition of hunting waterfowl, deer, and turkey year-round, there are plenty of opportunities for hunters no matter when you choose to get away. Great Oak Manor is centrally located near top hunting destinations and boasts beautiful … Read More

Honeymoons on the Eastern Shore

The honeymoon is a special time in a couple’s life. Finally brought together in harmony, your first vacation together will make memories that last a lifetime, so why not make your getaway extra special? With a honeymoon on the beautiful eastern shore, you and your partner will see the best that Chestertown has to offer! … Read More

Romantic outdoor hammock at Eastern Shore Inn

Celebrate Each Chapter of Your Love

Love is always in the air here at our eastern shore bed and breakfast, making it the perfect location to celebrate your relationship! Grab your lover and come experience a romantic getaway in Maryland at our waterfront property. Whether you’re planning to pop the question, commemorate your love with a gorgeous wedding or elopement, celebrate … Read More

Two women shopping in chestertown - walking into a store

Experience the Best Activities and Shopping in Maryland

When you stay with us you get much more than a wonderful place to stay, you get to experience everything the historic Chestertown, MD area has to offer during your Maryland vacation. While we offer numerous amenities and Inn activities, we encourage all of our guests to get out and explore the quaint town. Not … Read More

COVID-19 Travel Information

We’re working hard to keep our guests healthy and safe, and are continuing to monitor the Coronavirus situation. Please click below for the latest updates. We are here for you!

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