Great Oak Manor B&B in Chestertown Maryland
Great Oak Manor B&B Chestertown Maryland Bed and Breakfast Places To Stay Lodgings Accommodations

Host: Holly and Richard


Accommodations: 12

Address: 10568 Cliff Rd., Chestertown, Maryland 21620 USA

Telephone: (410) 778-5943,
1 800 504-3098

Activities/Attractions: Chestertown is host to a wide variety of activities sure to keep you busy for an entire day or more! Pick out farm fresh fruits and veggies at the farmers market, visit a local museum and learn all about the history of the area, browse a used bookstore at your leisure, or go wine-tasting. Conveniently located near the Inn, there’s no shortage of fun activities for those venturing into historic Chestertown.

The options for your vacation on the Chesapeake Bay waterfront at our Eastern Shore bed and breakfast are endless. You can do everything, or do nothing at all. In fact, relaxing is the point. While Great Oak Manor offers serene views and quiet relaxation, the surrounding area is full of attractions ready to be explored! Whether you want to be active or simply relax, the options are plentiful.

  •  Take a bicycle ride on safe country roads
  • Explore the water from our private beach by kayak, paddle board, or canoe
  • Walk from our beach to the marina next door where you have access to a swimming pool, a fitness center, and a nine-hole golf course
  • To slow down, relax in a hammock shaded by stately old walnut trees, sit by the bay in an Adirondack chair or stroll the expansive lawn
  • Be sure not to miss our spectacular sunsets

"All rooms are beautifully decorated and the setting is breathtaking."

"We recently spent our honeymoon in the Roese Suite, one of three that allow pets. We absolutely loved it! The staff was excellent and very knowledgeable in regards to the history of the property."

"Fantastic home and staff...very relaxing environment to unplug for the weekend. Food was fantastic."

"The manor is most impressive and is located in a beautiful setting, overlooking the Chesapeake, and surrounded by farm fields. It is a quiet, serene spot. Breakfasts were excellent. Our room was spacious and comfortable. Holly, our hostess, could not have been more gracious."

"This beautiful inn is all you could hope for and more. The inn is magnificent and the view breathtaking."

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. Features include:

  • 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
  • Comphy 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

Payment Accepted: Visa, MasterCard, Cash.

Rates: (Prices quoted in US Dollars)

From $159/night

Full Breakfast included.

"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."

"This is the place to relax! Holly, Richard and Cass are truly welcoming people who make you feel totally at home right away. What a difference to be around people who clearly love what they do."

"The property is stunning and we were welcomed personally and had a very nice personal tour."