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

Where to Eat Dinner (or Brunch) this Easter

This Easter, enjoy divine culinary experiences across Kent County. We’re not cooking this Easter (we need a break on at least one holiday!), but there are plenty of dining options on the Eastern Shore. Check out a few of our favorite spots: Barbara’s on the Bay Betterton, MD Open for Brunch from 10:30 a.m. to … Read More

Letter from the Innkeeper – February

So here it is February already and our thoughts turn to love and celebrations of love. There are so many kinds of love to express. Richard and I have been at Great Oak Manor for 11 months now and we just love this place. What is not to love about sitting at one’s desk or … Read More