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

chester river co Cruising

Top 10 Summer Activities in Maryland

Summer is one of our favorite times of the year. The foliage and flowers are in full bloom, the weather is fantastic and the adventures to enjoy are plenty. Below is our list of the top 10 adventures to enjoy throughout the Eastern Shore. Join us at our top-rated waterfront Maryland bed and breakfast and … Read More

Couple on a yacht holding the mast with their arms splayed out

Springtime on the Eastern Shore : A 3-Night Itinerary

Nothing is quite like springtime in New England. The weather is mild, the flowers are blooming, and the outdoor adventures are available for you to enjoy. Right now is a great time for a getaway to Chestertown, MD. To make it easier, we’ve put together this handy itinerary so you can spend less time planning … 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

Three Women on the Beach wrapped in a blue and orange plaid blanket

Plan a Girls Getaway to the Chesapeake Bay

When is it a good time to plan a girls getaway to the Chesapeake Bay at Great Oak Manor? The answer is NOW! This time of year you are spending lots of quality time with your family. But when you’ve had it “up to here” with them, you’ll need time away with your girlfriends to … Read More

Holiday Wine Bottles for an East Coast Holiday

A Magical Eastern Shore Holiday Season

With the holiday season right around the corner, it’s the perfect time to plan a little R&R into your busy schedule for a mid-season pick-me-up for this year’s festivities. Great Oak Manor on the Chesapeake Bay is the perfect destination for a magical East Coast Holiday. Join us at our waterfront Chestertown, Maryland bed and … Read More

Young Couple Biking in the sunshine

Adventures by Land and Water in Maryland

Our magnificent country estate on Maryland’s Eastern Shore offers stunning views of the Chesapeake Bay and is located minutes away from Chestertown. Be as active as you’d like, or simply relax – the options are plentiful. If you’d like a little adventure, read on to learn about some of our favorite outdoor activities – on land … Read More

Romantic couple about to kiss by the water at sunset

Romance on the Eastern Shore

The Perfect 3 Days Away Whether you’re celebrating a honeymoon, anniversary, birthday, or simply being in love, Chesapeake Bay is an ideal destination for romance, and Great Oak Manor is the perfect setting for your special occasion. Want to get away with your one and only? All you have to do is select your favorite … Read More