This country estate provides the ultimate waterfront setting for a relaxing and romantic getaway. You'll be surrounded in comfort and luxury from the estate's walled garden to its private beach with a magnificent view of the Chesapeake Bay. Enjoy the outdoors with our complimentary cruiser bikes, kayaks, paddle boards, hammocks, binoculars, fire-pit and more. Guest rooms and public spaces are luxuriously furnished and comfortably spacious. We are a true Manor House with fine details, quality furnishings, Oriental rugs, and an 850-volume library of books. The high speed Wi-Fi and 1,200 ft. of waterfront lawn on the Chesapeake Bay just add to the charm and modern amenities offered. Start your day with a full gourmet breakfast to be enjoyed in the dining room or on the patio overlooking the water. Join us at our waterfront Chestertown, MD bed and breakfast to experience the most comfortable accommodations, beautiful sunsets, and superb service on the Eastern Shore of Maryland.
Inn Amenities: Free Onsite Parking, Gardens on Property, LGBT Friendly, Green Environmentally Friendly, Limited Spa Service, Tesla/Electric Vehicle Charging Station, Wine/Spirits Available,
Food & Wine
Private dining is an option. Crab feast package available.
Meals Offered: Breakfast
Restaurant on Premises: No
Special Diets Accomodated: Yes
Breakfast Service: Full
Breakfast Seating: Individual Tables , Set Times
Dining Amenities: Complimentary Beverages , Complimentary Afternoon Tea/Refreshments , Complimentary Snacks , Complimentary Early Coffee Tea , Evening Cocktails , Picnics Available
Rooms & Suites
At our waterfront Eastern Shore Bed and Breakfast, our 12 guest rooms offer the ultimate in luxury and comfort. Each of the rooms feature their own private bathrooms, unique décor, modern amenities, Wi-Fi, beautiful views and luxurious linens. Some individual room highlights include cozy fireplaces, balconies, skylights and French doors. Our newly added Carriage House can sleep six, has a full kitchen, living area and majestic views of the Chesapeake Bay. When not in your room, our beautiful common areas are a wonderful place to enjoy games, reading or conversation. A full breakfast, afternoon snacks and evening cordials are included each day during your stay.
Accommodations: Apartments, Suites
# of Rooms: 13
Beds: Twin, Queen, King
Room Entertainment: Cable TV
Safes: Front Desk
Handicap Accessible: Limited
Room Amenities: Air Conditioning, Alarm Clocks, Antique Furnishing, Bathrobes, Fireplace, Hair Dryer, Ironing Boards, Private Deck, Rollaway Available
Guests enjoy a full breakfast, afternoon snacks and evening cordials. Great Oak manor provides complimentary bikes, beach access, kayaks, paddle boards, binoculars and more to get out and enjoy the top Chesapeake Bay activities.
Internet Service: Wired, Wireless, Complimentary
Front Desk/Security: OnSite
Corporate Rates: Yes
Inn Amenities: Free Onsite Parking, Gardens on Property, LGBT Friendly, Green Environmentally Friendly, Limited Spa Service, Tesla/Electric Vehicle Charging Station, Wine/Spirits Available
Location Type: Waterfront, Waterview
Minimum Stay Required: Weekends, Holidays
Pet Friendly: Yes
Innkeeper's Pets: Inside
Smoking Policy: Only in designated areas
Family Friendly: Over 12
Weddings & Events
Whether you're planning an intimate elopement or waterfront wedding, our Chesapeake Bay wedding venue provides the perfect setting for your special day. With a select list of the area’s finest caterers and chefs, your gracious hosts will take every step to ensure your event is a memorable one at our Eastern Shore bed and breakfast.
Wedding/Events Capacity: 100-199
Events Supported: Private Parties, Ceremony, Receptions, Rehersal Dinner, Elopment
Wedding/Reception/Event Facilities: Indoor, Outdoor
Reception Seating: 75
Banquet Seating: 75
Max Capacity Outdoor: 250
Business Travel & Events
Our Chesapeake Bay event center is the perfect getaway location for corporate retreats and meetings. The large open space of the Conservatory is a favorite place to gather. The view of the Chesapeake, high speed Wi-Fi and convenient restrooms make it an ideal place to host your guests. We can furnish tables and chairs for small groups. Our 12 guest rooms and Carriage House provide convenient accommodations for those traveling from out of the area at our waterfront bed and breakfast on Maryland's Eastern Shore.
# of Meeting Rooms: 3
Meeting Types: Business Meeting, Retreats, Social
Meeting Amenities: Onsite Catering
Meeting Facilities: Indoor, Outdoor
Business Travel & Event Max Capacity: 60
Total Rooms Sq Footages: 2200
Max Capacity Boardroom: 24
Max Capacity Classroom: 24