Great Oak Manor

Great Oak Manor

10568 Cliff Rd
Chestertown, MD 21620
United States
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Toll Free (800) 504-3098 ; Local (410) 778-5943
Average rate/night $182
Check Availability *Rooms starting at 159.00

F. Scott Fitzgerald wrote of blue lawns and country houses such as Great Oak Manor. From the estate's walled garden bordered by 65-year old boxwoods and its circular drive on the estate side, to its magnificent view of the Chesapeake Bay and private beach on the water side, this country estate provides the appropriate setting for a relaxing getaway and a weekend of romance. Guest and public rooms are spacious, beautifully furnished and comfortable. A true Manor House with fine details, beautiful furnishings, Orientals, and an 850-volume library to browse, high speed WIFI access, plus 1,200 ft. of waterfront lawn on The Cheasepeake Bay, and the most beautiful sunsets on the Eastern Shore of Maryland. Each guest at our Chestertown, MD bed and breakfast will receive a lovely hot breakfast in the dining room overlooking the water. Join us at the waterfront inn on the Chesapeake.


  • Inn Amenities Refine Search: Free Onsite Parking, Gardens on Property, Wine/Spirits available
  • Member Since: 2003


  • Minimum Stay Required: Weekends, Holidays
  • Inkeepers Pets: Inside
  • Pet Friendly: Yes
  • Smoking Policy: Only in designated areas
  • Family Friendly: Yes, Over 12

Food & Wine

Private dining is an option

  • Meals Offered: Breakfast
  • Breakfast: Complimentary
  • Breakfast Seating: Individual Tables, Set Times
  • Breakfast Service: Full
  • Complimentary Breakfast: Yes
  • Offered Amenities: Complimentary Beverages, Complimentary Afternoon Tea/Refreshments, Complimentary Snacks, Complimentary Early Coffee/Tea
  • Special Diets Accommodated: Yes
  • Restaurant on Premises: No
  • Pub/Tavern on Premises: No

Rooms & Suites

There is a special place just waiting for you on the Chesapeake Bay on Maryland’s Eastern Shore. Located minutes away from Chestertown, Great Oak Manor is a magnificent country estate built in the Georgian Style. It is a charming Bed and Breakfast with twelve guest rooms and a fabulous family style accommodation in addition to spacious common areas. Each of the rooms feature their own unique decor with individual highlights such as a cozy fireplace, a spacious bath with skylight, inviting French doors leading to the garden, or a rich red bathroom and modern amenities.

  • Accommodations: Apartment, Suites
  • # Rooms: 13
  • Beds: Twin, Queen, King
  • Room Amenities: Air Conditioning, Antique Furnishings, Bathrobes, Fireplaces, Hair dryers, Private Deck, Rollaway Available, Alarm Clocks, Ironing Boards
  • Entertainment: Cable TV , Video Library
  • Safes: Front Desk
  • Handicap Accessible: Limited
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Guest Services

  • Internet Services: Wired, Wireless, Complimentary
  • Corporate Rates: Yes
  • Front Desk/Security: Onsite
  • Inn Amenities: Free Onsite Parking, Gardens on Property, Green/Enviromentally Friendly, Limited Spa Services, Tesla/Electric Vehicle Charging Station, Wine/Spirits available

Location Type

  • Location Type: Coastal, Waterfront, Waterview, Small Town/Village

Weddings & Events

Throwing a bouquet or throwing a banquet? Black-tie or tie-dye? No matter what you’re planning, a wedding, corporate event or a reunion party, the shores of the Chesapeake are the perfect setting for your next event. With a select list of the area’s finest caterers and chefs, your gracious hosts will take every step to ensure your party is a memorable one.

  • Weddings & Events Capacity: 100-199
  • Events Supported: Private Parties, Ceremony, Receptions, Elopement
  • Wedding/Reception/Event Facilities: Indoor, Outdoor
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Business Travel & Events

Great Oak Manor is the perfect getaway location for corporate retreats and meetings. The large open space of the Conservatory is a favorite for these meetings with a view of the Chesapeake. Wi-Fi and close restrooms make it ideal. We can furnish tables and chairs for small groups.

  • Banquet Seating: 75
  • Reception Seating: 75
  • Max Capacity Outdoor: 250
  • Max Capacity Classroom: 24
  • Max Capacity Boardroom: 24
  • Business Travel & Events Max Capacity: 60
  • Total Rooms Sq Footage: 2200
  • Total Meeting Rooms: 3
  • Meeting Facilities: Indoor, Outdoor
  • Meeting Amenities: Onsite Catering
  • Meeting Types: Business Meeting, Retreats, Social
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