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
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
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
Elizabeth Barrett Browning may inspire you to say, “How do I love thee? Let me count the ways.” But as you’re planning your wedding day, maybe you should be asking, “Where is the best place to get married on the Eastern Shore?” The answer is Great Oak Manor, and we’ve counted the ways for you! … Read More
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
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
Sometimes the fantastic food is the real reason you visit Maryland’s Eastern shore, and all of the fun outdoor activities are just icing on the crab cake! The area around our waterfront Inn offers such a wide variety of locally sourced and professionally crafted cuisine and libations that you’re certain to find a new favorite. … Read More
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
