Photo of Great Oak Manor

“A charming and historic waterfront inn set on a country estate near Chestertown. Rooms are spacious and elegant with antique furniture, skylights, cosy fireplaces and stand-alone tubs. Relax in a hammock shaded by stately old walnut trees or use the paddleboards, kayaks and bicycles. A homely stay.”

“A charming and historic waterfront inn set on a country estate near Chestertown. Rooms are spacious and elegant with antique furniture, skylights, cosy fireplaces and stand-alone tubs. Relax in a hammock shaded by stately old walnut trees or use the paddleboards, kayaks and bicycles. A homely stay.”

Recommended For

  • Back to Nature
  • Enjoy the outdoors with the inn's complimentary cruiser bikes, kayaks, paddle boards, hammocks, binoculars, fire-pit and more
  • Other Activities
  • Drive the National Scenic Byway, that takes you through historic towns, fishing and boating spots, and gorgeous natural scenery
  • Wine tasting
  • The inn is on the Chesapeake Wine Trail with many wineries just a matter of minutes away
  • Cycling
  • The inn provides cruiser bicycles (4 available) as well as a biking tour map
  • Local markets
  • Visit Chestertown's Farmer’s Market which opens every Saturday morning
  • Sailing
  • Go on sunset cruise and spot dolphins
  • Self catering to rent
  • Newly added Carriage House can sleep six, has a full kitchen, living area and majestic views of the Chesapeake Bay
  • Pet friendly
  • Dogs receive a cosy bed, warm blanket, feeding & water bowl, fun toys and tasty treats
  • Restrictions on children
  • Children over the age of 12 are welcome
  • No restaurant
  • Breakfast is served
  • Romantic
  • Wedding license
  • Eco
  • Beach nearby
  • Antiques
  • B&B
  • Lakeside

Facilities

  • Self catering to rent
  • Newly added Carriage House can sleep six, has a full kitchen, living area and majestic views of the Chesapeake Bay
  • Pet friendly
  • Dogs receive a cosy bed, warm blanket, feeding & water bowl, fun toys and tasty treats
  • Restrictions on children
  • Children over the age of 12 are welcome
  • No restaurant
  • Breakfast is served
  • Private chef / butler
  • Bicycles available
  • Wedding license
  • Parking
  • Bath robes
  • Safe
  • Air conditioning
  • Wifi
  • Satellite / Cable TV
  • Concierge
  • Suites
  • Garden

Activities

  • Other Activities
  • Drive the National Scenic Byway, that takes you through historic towns, fishing and boating spots, and gorgeous natural scenery
  • Wine tasting
  • The inn is on the Chesapeake Wine Trail with many wineries just a matter of minutes away
  • Cycling
  • The inn provides cruiser bicycles (4 available) as well as a biking tour map
  • Local markets
  • Visit Chestertown's Farmer’s Market which opens every Saturday morning
  • Sailing
  • Go on sunset cruise and spot dolphins

Map & Location

What's Nearby