Online Bookable Property

Rooms available starting from $185.71   

Great Oak Manor

One of Maryland's historically significant estates, Great Oak Manor sits on twelve acres directly on the Chesapeake Bay in Maryland's Eastern Shore, eight miles from historic Chestertown. With large common rooms and beautifully appointed guest rooms, comfortable outside seating areas shaded by majestic Oak and Walnut trees, the Manor affords its guests ample and comfortable areas in which to relax.

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Location

  • Location is best described as:
    • Golf Course
    • Marina
    • Beachside
    • Countryside
    • Small town
  • Nearest major city: Chestertown, MD (8 miles south)
  • Directions to property:
    Visit Web Site
  • Nearest major airport: Baltimore, MD (BWI-Baltimore Washington) 65 miles
  • Directions from airport:
    Philadelphia International is also within 90 minutes. Detailed directions provided with confirmation.

Room Rates (USD American Dollars)

All occupancy rates are subject to change
  • State and local taxes may apply
  • Accommodations: Lrg. Rooms w/ king beds
  • There are 12 guest accommodations (12 with private baths)
  • Single occupancy rate is between $ 165.00 and $ 310.00
  • Double occupancy rate is between $ 165.00 and $ 310.00
  • The rate for each additional person is $ 50.00
  • Other Accommodations: Roese Suite
    Rate are for double occupancy as there is no single occupancy rate available. Rates are adjusted seasonally and the ranges are for high season April 15th - November 1st, and November 2nd - April 14th. Please call for reservations and romantic packages.

Amenities

In Room
  • Air conditioning
  • Alarm clock
  • Amenities Basket
  • Bath robes
  • CD player
  • Coffee/Tea facilities
  • DVD Player
  • Data port
  • Desk
  • Fireplace
  • Hairdryer
  • Internet Service
  • Ironing Board
  • Radio
  • TV
  • Telephone
  • Turndown Service
  • VCR
  • On Site
  • Board games
  • Ceiling fans
  • Conference Rooms
  • Copier
  • Fax Machine
  • Library
  • Piano
  • Satellite/Cable TV
  • Videos
  • Wedding Facilities
  • Wet bar
  • Other Amenitites
  • Room safes
  • Bicycles
  • Golf
  • Swimming
  • Indor exercise pool
  • Tennis
  • Meals

    • A Full buffet with hot entree breakfast is included with room rate
    • Breakfast is served from: 8:30 am to 10 am
    • Breakfast is served in the waterside terrace, Dining Room
    • Lunch is available by special request
    • Dinner is available by special request
    • Additional food services included in room rate: bottled water, evening port & sherry, fresh fruit, soft drinks, Afternoon tea, Fruit, Non-alcoholic beverage
    • Special meals available: check our specials, Low Fat, Restricted, Vegetarian
    • Our signature dish is Crab Quiche
      Our Breakfast buffet has seasonal fresh fruit, homemade muffins and breads, cold cereal, yogurts and a hot entree'. Depending on the day, you may be served either French toast and sausage, crab quiche or quiche Lorraine, eggs and ham to order, your preference, or an egg strata.

    Policies

    • Minimum stay required (Holidays weekends and Stays Over most Saturdays, two night min.)
    • Smoking is allowed in limited areas (Terrace outside)
    • We cannot accommodate guest pets
    • Limitations on children staying (children under 17are welcome for family events, weddings,etc)
    • No childcare is provided
    • Consumption of alcohol is permitted (Evening Port and sherry, or you may bring your own)
    • Deposit amount required (One night deposit will be charged to your credit card at the time of reservation. 50% for 3 or more nights.)
    • Closed: Thanksgiving and Christmas
    • Check in time is 3 pm and Check out time is 12 noon
    • Cancellations:
      Cancellation must be made no later than 14 days prior to your arrival date. Cancellation made after 14 days, will be charged one night's rate at the highest rate to your credit card. If your accommodations can be resold, a $25 cancellation fee will replace the one night rate cancellation mentioned above. There is a $25 fee no matter when you cancel
    • Accepted by the following agencies:
      • Kent County Lodging Association
      • MBBA
      • Professional Association of Innkeepers International
      • Select Registry
      • Chamber of Commerce

    Discounts available:
     10%Active Duty Military 
     10%Corporate 
     10%Group 
     10%Seniors 65 and Older 

    Innkeepers

    • Innkeeper(s): Cassandra Fedas
    • The innkeepers speak: English
    • There are 3 cats on the property
    • Other pet(s) on the property: kept in Owners Quarters

    Area Attractions

    Antique Shopping, Art Galleries, Beach, Concert venue, Gourmet/Fine Dining, Historical interests, Lake, Live Music, Movie Theater, Museum, National/State parks, Nature area, Chesapeake Bay, Wildlife Refuge, Historic Washington College, Historic Churches, Outlet Stores, Performing Theater, Picnic area, Religious Services, River

    Onsite or Nearby Activities

    Bicycle riding trails, Bicycles, Bird watching, Boating, Canoeing, Fishing, Golfing, Hiking trails, Horseback riding, Horseshoes, Hunting, Kayaking, Nature Trails, Sunset Cruises, Sporting Clays, Sailing, Shopping, Sight-seeing, Swimming, Swimming pool, Tennis courts, Tennis racket rental, Water sports

    Online Bookable Property

    Rooms available starting from $185.71   

    Contact Information


    Great Oak Manor Bed and Breakfast
    Great Oak Manor
    10568 Cliff Rd
    Chestertown MD 21620-4115
    USA
    Phone: +1-410-778-5943
    Fax: +1-410-810-2517
    Toll-free: +1-800-504-3098
    Innkeeper(s)
    Cassandra Fedas
    Rates:
    $165 - $310
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    Online Reservations

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    Reviews

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    Read all 16 Reviews
    Review Great Oak Manor, Chestertown, MD

    Photo Album

    Great Oak was built at a time when grandeur was more important than cost, when craftsmen were artisans and when houses were built to last for generations to enjoy. 

The Manor was built in the tradition of the 18th Century with bricks from the ballast of W.R. Grace sailing ships. 

A relaxing and memorable Bed & Breakfast on Maryland's Eastern Shore.A great getaway. The Chesapeake room is one of six common rooms available to our guest, for evening Port and Sherry, reading one of our 825 books, games, TV or movie watching, or simply relax by a winters fire.
    The Conservatory, with west facing glass enclosure you can view the sunsets year round.Sitting with views of the bay, 
this elegant fireplace dining room features 
a full breakfast with Manor-baked muffins, hot entree, cereals, yogurts, and always fresh fruit.
   Welcome!
    The Marmaduke Room - named for the first land grantee from Lord Baltimore overlooks the bay and is one of our deluxe waterviews with a king bed, sitting area, private bath and fireplace.D'Oench a deluxe waterfront room with king bed, fireplace expansive water views, sitting area, large private bath, and like all of our rooms equiped with luxury bathrobes hair dryers, irons and ironing boards. Come and relax.
    Hodges, with a four posted queen, fireplace and large private bath is a great estate setting at a reasonable price.The Roese suite is two rooms. One with a king bed and writing area with desk. The other is a gracious living room with fireplace, sofa and sitting area with television and lots of light. The cathedral ceiling private bath and walk in closet add to this suites elegance.
    The Roese suite is two rooms. One with a king bed and writing area with desk. The other is a gracious living room with fireplace, sofa and sitting area with television and lots of light. The cathedral ceiling private bath and walk in closet add to this suites elegance.

    Features

    Property Noted For:
    • Corporate Retreats
    • Family Reunions
    • Small Weddings
    • Antiques/decor
    • Business travel
    • Excellent views
    • Fitness
    • Group events
    • Honeymoons
    • Luxury
    • Nature
    • Peaceful getaway
    • Romantic escape
    • Weddings

    Type:
    • Waterfront Estate
    • Bed and Breakfast
    • Country Inn
    • Historic Inn

    Details:
    • Architectural style is Georgian
    • Built in 1938
    • Opened for business in 1952
    • Restored / Remodeled in 2003
    • Access for the disabled is limited
    • Parking available