Great Oak Manor

Select Registry member since 2003
Casual Elegance on the Chesapeake Bay
10568 Cliff Rd Chestertown, MD 21620
Great Oak Manor
Gourmet Breakfast
Exterior Day time
Kayak on our Private Beach
Lake View from the Deck
Carriage House Master Bedroom
Hammock with a View
Marmaduke Bedroom
View at Dusk
Great Oak Manor Sunset
Great Oak Manor Fire Pit
Great Oak Manor Crab Feast
Great Oak Manor Bikes
Great Oak Manor Common Areas
Chesapeake Bay Weddings

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.

Checking for available rooms...


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 Accommodated: Vegetarian , Vegan , Gluten Free , Yes

Breakfast: Complimentary

Breakfast Service: Full

Breakfast Seating: Individual Tables , Set Times

Alcohol Permits: Beer , Wine , Spirits

Dining Amenities: Complimentary Beverages , Complimentary Afternoon Tea/Refreshments , Complimentary Snacks , Complimentary Early Coffee Tea , 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: Queen, King

Room Entertainment: Cable TV, iPod Docking Statio

Safes: Front Desk

Handicap Accessible: Limited

Room Amenities: Air Conditioning, Bathrobes, Fireplace, Hair Dryer, Ironing Boards, Rollaway Available

Guest Services

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: 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

Location Type: Waterfront, Waterview


Minimum Stay Required: Weekends, Holidays

Pet-Friendly: Yes

Innkeeper's Pets: Inside

Smoking Policy: Outside Only

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, Rehearsal Dinner, Bridal Luncheon, Elopment

Wedding/Reception/Event Facilities: Indoor, Outdoor

Reception Seating: 75

Banquet Seating: 75

Max Capacity Outdoor: 200

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: 25

Total Rooms Sq Footages: 2200

Max Capacity Boardroom: 24

Max Capacity Classroom: 24

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