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

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

Great Oak Manor Bride and Groom kissing

A Love Story featuring the Best Wedding Venue in Maryland

Throughout every season we have the opportunity to work with so many lovely couples when they host their special day at our outdoor wedding venue in Maryland. Each one filled with so much love and excitement as they walk through our doors to plan their I Do’s. As wedding season swings into full effect, we … Read More

A Blog from Lizzie the Dog: A Maryland Pet-Friendly Vacation

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

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

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