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 $149.17
Check Availability *Rooms starting at 139.00

F. Scott Fitzgerald wrote of blue lawns and country houses such is 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.

Policies

  • Minimum Stay Required: Weekends
  • Inkeepers Pets: Inside
  • Pet Friendly: Yes
  • Smoking Policy: Smoke-Free
  • Family Friendly: Yes

Other

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

Food & Wine

  • Meals Offered: Breakfast
  • Breakfast: Complimentary
  • Breakfast Seating: Individual Tables
  • 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

Great Oak Manor provides more than a place to sleep. Located on the Chesapeake Bay, we offer a place to dream. Make yourself comfortable as you take a look at each one of our guest rooms in this Chestertown, Maryland luxury waterfront inn. Rest amongst the softest sheets on comfortable beds. A luxury robe awaits your arrival—as well as bottled sparkling water, a light snack, and the finest bath and shower amenities .Great Oak Manor provides more than a place to sleep. Located on the Chesapeake Bay, we offer a place to dream. Make yourself comfortable as you take a look at each one of our guest rooms in this Chestertown, Maryland luxury waterfront inn. Rest amongst the softest sheets on comfortable beds topped with down featherbeds. A luxury robe awaits your arrival—as well as bottled sparkling water, a light snack, and the finest bath and shower amenities .

Every morning is not only met with stunning views of the Chesapeake, but also a hot breakfast buffet with seasonal fresh fruit, homemade muffins, cold cereal, and a hot entrée, such as French toast, quiches or egg strata, is always offered. Enjoy your breakfast in the dining room, amongst much silver and china, or take it out to the terrace for a better view of the bay.

The Marmaduke;

Rise to breathtaking views of the bay from a king-sized bed that begs you to stay under the covers for a moment longer. Bright and airy, the Marmaduke features rich floral hues and chairs perfect for reading or gazing at the view. With a cozy fireplace, walk-in closet and sumptuous bath with soaking tub, this luxury guest room is as lovely as the first land owner for which it is named.

  • Accommodations: Apartment, Suites
  • # Rooms: 13
  • Beds: 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, 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

  • Banquet Seating: 75
  • Reception Seating: 75
  • Max Capacity Outdoor: 150
  • 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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