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

Black and White photo of bride and groom at a tent reception

7 Reasons to Get Married on the Eastern Shore at Great Oak Manor

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

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

Fireworks on the 4th of July

Fourth of July Festivities on the Eastern Shore

It’s not often that Independence Day celebrations last all week, but that’s the case this year in Kent County, Maryland! Spend an entire week at Great Oak Manor on the Chesapeake Bay to enjoy THREE nights of fireworks and other fun festivities throughout the County. Start your week in Rock Hall on July 1 to … Read More

Mother's Day gift and flowers

Mother’s Day on the Bay

Mom does it all for us – from packing lunches to homework to help to watching our own babies when we need a night out. Mother’s Day is the perfect opportunity to show mom just how much you care for her and appreciate all she does for you. This year, let her escape to Maryland’s … Read More

Couple and their dog watching the sunset over the water

A Letter from the Innkeepers – April 2018

  Spring is here – well, almost here. This time last year we were just settling in and rushing around to make spring happen. This year we are super excited about some wonderful changes that are taking place around here. Richard has been working all winter on the inside of the Manor, painting and sprucing … Read More