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

A woman relaxing in a hammock at Maryland hotel

Staycation: The Perfect Maryland Vacation at our Chesapeake Bay Hotel

Life involves a lot of planning. We plan out our days, our nights, and every facet of our lives to ensure that things continue to run smoothly. A life more organized is certainly not a bad thing, but all that scheduling can certainly start to weigh you down. Unfortunately, the classic solution to get away … Read More

A Blog from Lizzie the Dog: A Maryland Pet-Friendly Vacation

One of the hardest parts about going on vacation is having to leave your furry ones behind. Luckily, here at our beautiful Chestertown, MD bed and breakfast, we understand pets are like family and want you to bring yours along! Don’t just take it from us, hear what our sweet pup Lizzie has to say … Read More