Great Oak Manor B&B in Chestertown, Maryland

Hosts: Holly and Richard – Rates: ($USD): From $159/night – Accommodations: 12 guest rooms – Address: 10568 Cliff Rd, Chestertown, Maryland 21620 USA – Telephone: (410) 778-5943, 1 800 504-3098 – Website

Great Oak Manor B&B in Chestertown, Maryland Great Oak Manor B&B in Chestertown, Maryland Fireplace Great Oak Manor B&B in Chestertown, Maryland Bedroom

General Information: Welcome to Great Oak Manor in Chestertown, Maryland … a special place just waiting for you on the Chesapeake Bay on Maryland’s Eastern Shore. Our charming, Georgian style B&B has twelve guest rooms in addition to spacious common areas. We invite you to take full advantage of our luxurious accommodations.

Enjoy your full breakfast in the Bay View Dining Room. Explore the books in the Library. Relax in the Sunroom and drink a cup of tea or coffee, always available 24 hours a day. Indulge daily in a sweet and savory afternoon snack, and nap in the hammocks or Adirondack chairs on the bluff. When you return from dinner, look forward to the complimentary Port and Sherry in the Music Room.

  • Private bathrooms with complimentary shampoo, conditioner and body wash and Turkish towel linens
  • Hair dryers
  • Flat screen, high definition televisions
  • DIRECTV with HBO
  • Wi-fi
  • Comfy bed linens
  • Robes
  • 6 guest rooms have fireplaces
  • Cruiser bicycles
  • Kayaks, canoe, and paddle boards
  • Waterside firepit
  • Patio firepit
  • Private Chesapeake Bay beach access
  • 2 Tesla charging stations
  • Cornhole
  • Binoculars for bird watching

“Stunning property and accommodations. The grounds have so much to offer and breathtaking views of the bay. Quaint and serene are a perfect description for the manor.”

“I have now been to Great Oak four times and love it all the more each time. It has become my go-to getaway.”

“This is our second stay at Great Oak and we will be back. Holly and Richard are excellent hosts and made us feel like family.”

The Great Oak Manor is a beautiful mansion with a lawn that extends 100 yards down to the water. The house is beautiful, the rooms are very nice, the bed is very comfortable and the breakfast is delicious. Holly and Joe are very nice and accommodating.”

The location is spectacularly scenic! The building is impeccably furnished and appointed! The entire “package” of building and grounds is superbly maintained.”