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

Great Oak Manor Bride and Groom kissing

A Love Story featuring the Best Wedding Venue in Maryland

Throughout every season we have the opportunity to work with so many lovely couples when they host their special day at our outdoor wedding venue in Maryland. Each one filled with so much love and excitement as they walk through our doors to plan their I Do’s. As wedding season swings into full effect, we … 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