Staycation: The Perfect Maryland Vacation at our Chesapeake Bay Hotel

Life involves a lot of planning. We plan out our days, our nights, and every facet of our lives to ensure that things continue to run smoothly. A life more organized is certainly not a bad thing, but all that scheduling can certainly start to weigh you down. Unfortunately, the classic solution to get away from it all, a vacation, sometimes makes it worse! A trip intended to be a relaxing getaway can quickly spiral into even more planning and easily turn a vacation intended to relieve the stresses of life into yet another exhausting venture with little time for rest and recuperation. Luckily, there is a better way that ensures your trip from reality stays as relaxed as possible. Whether it’s a weekend getaway from DC or a staycation in town, you can truly experience an uncomplicated and worry-free Maryland vacation at Great Oak Manor.

Night view of Great Oak Manor, wedding venue in Maryland

Luxury Chestertown Bed and Breakfast

Everything you need for the perfect stay is provided at our luxury Chesapeake Bay hotel. Enjoy high-quality amenities and top-notch service without ever having to leave the property. Our bed and breakfast sits on several acres of land and provides a fantastic view of the water as our land backs up right to the Chesapeake Bay! Of course, a full breakfast is also provided and includes delicious favorites like fresh eggs and thick-sliced, applewood smoked bacon. If you’re looking to make your trip extra special, we offer a number of premium enhancements including:

– A private dinner for two

– Delicious cheese plates delivered to your room

– 60-minute massages or reflexology sessions

A Great Oak Manors Guest Dog on Chesapeake Bay

You Can Bring Your Pup

Great Oak Manor prides itself on being one of the best pet-friendly hotels in Maryland. Feel free to bring your furry friend along with you and give your dog a vacation too! With plenty of room to run around, there’s no better place for canine relaxation. Make sure and check out our special pet-friendly page for more information.

Kayak and chairs on the beach at our Cheaspeake Bay B&B

Fun Summer Packages

Have a wonderful romantic evening or enjoy a delicious crab-eating experience at your leisure, both are available without ever having to leave the property! Our most popular package is the Romance Package and has everything you need for the perfect date night as it includes these fun treats:

– A floral arrangement

– Chocolate truffles

– Complimentary sparkling wine

The Crab Feast Package, also a guest favorite, is an absolute delight for the senses and palate. This yummy meal comes with:

– One dozen steamed crabs

– Corn on the cob

– Your choice of complimentary beer or wine

– Held in your own private gazebo overlooking the bay

Russell Suite bed and seating area with fireplace

Unique and Comfortable Lodging

What would a comfy stay at Great Oak be without our wonderful rooms? Each suite showcases the hotel’s design aesthetic with bold, dark colors and a distinct New England influence. One of our favorite rooms is the Russell Room, with its gorgeous red carpeting, a spacious king bed, fireplace, and its morning bay sunrise views.

Another favorite is the Sterling Room which includes the same amenities as the Russel Room, with the addition of a private entrance, pet-friendly quarters, and is wheelchair accessible.


Summer Tip: Make sure and check out our Summer Midweek Sale which offers discounts for guests staying in the Carriage House this June.

Enjoy a break from the planning of daily life with a weekend getaways in Maryland! Come into the new week refreshed and ready to get back on schedule, but not before enjoying some of the highest quality accommodations in the area. All you have to do is make the trip and we’ll take care of everything else, leaving you with more time to relax and enjoy quality time away from it all. Come and see what makes us stand out from the rest and experience a vacation unlike any other.