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

Intimate “I Dos” at Great Oak Manor

Love is a beautiful thing. Bringing people together as nothing else can, it has defined the human experience since time immemorial. Great Oak Manor celebrates this legacy with our exclusive elopement packages. For those seeking a smaller, more intimate ceremony by the beautiful waters of the Chesapeake Bay, we have the amenities to make your … Read More

Rent Out Great Oak Manor: Weekend Packages

Great Oak Manor is a charming Georgian estate located on the Eastern Shore, just minutes from historic Chestertown. No matter the season, Kent County offers beautiful scenery and plenty of fun attractions for you and your friends or family, including wine tours, bird watching (visit the tundra swan that drops by the Chesapeake Bay during … Read More

Enjoy a Delicious Thanksgiving Feast at Great Oak Manor

The holidays are a great time to take a few minutes to be grateful for those people and moments that we’ve had the pleasure of experiencing in our lives. While it may be a great time to reflect or catch up with old friends, they’re definitely not relaxing. From meal planning to gift buying (and … Read More

Celebrate the 2017 Holidays at Great Oak Manor

Holidays can often be stressful affairs between the gift giving, cooking, and cleaning. Why not treat yourself to a break this season and spend Thanksgiving or Christmas on Maryland’s Eastern Shore. Imagine waking up in the morning knowing you don’t have to cook and enjoying all the holiday splendor the Chesapeake Bay has to offer. … Read More

Winter Events at Great Oak Manor

Winter is upon us, and you may be feeling all of your daylight hours are wasting away in the office.  While it can be tempting to spend those chilly weekends huddled up at home watching Netflix (hey, we’ve all been there), why not do something different with your precious weekend time? Studies show that vacations, … Read More

Yoga, Thanksgiving, Massages, and More!

We’ve recently begun sending out a Mid-Month Manor Message to all of our newsletter readers as a way of highlighting some of our upcoming events and specials. If you missed out on our last one, have no fear! Just keep reading to find out about three ways that Great Oak plans to make your stay … Read More