Great Oak Manor Inn

Chestertown, MD Bed and Breakfast

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$189 - $315 Website Check Availability
  • Innkeeper: Kaylin and Scott Benfeild
  • Rooms: 12 Bathrooms: 12
10568 Cliff Road
Chestertown, MD 21620

A Select Registry Inn,
Approved by Maryland Bed and Breakfast Association.

Come for a getaway to Historic Great Oak Manor overlooking the Chesapeake Bay on Maryland’s Eastern Shore. Set on 12 acreas with private beach, complimentary bicycles,
just 1.5 hour driving time from Baltimore, Washington or Philadelphia. DISCOUNTS AND SPECIALS ON OUR WEB SITE

Featured in the Washington Post ” Escapes” Feb.2010 and on The Today Show in July 2005. We have also been featured in Southern Living February 2004, “A Country Hideaway,” Washingtonian Dream Weekend April 2003, Chesapeake Life’s 1999 Winter edition “Great Gatsby on the Chesapeake”.
Recognized by American Historic Inns as one of their “Top Ten Most Romantic Inns” .


  • Air Conditioner
  • Cable Television
  • Ceiling Fans
  • Coffee Maker
  • Private Bath


  • Children Under 17 Welcome
  • Inquire for Pets
  • Open All Year
  • Smoking Permitted On Grounds


  • Hors D'oeuvres
  • Off-Street Parking
  • Porch / Deck / Patio
  • Snacks / Beverages
  • Inspected By: Select Registry, Maryland B&B Association
  • Featured In: Baltimore Sun, Washtonian, Philadelphia Magazine, Southern Living, Chesapeake LifeWashington Post
  • Payment Types Accepted: Visa, MC, Amex, DiscoverCash, Check
  • Deposit: one night
  • Check In: 3:00 PM
  • Check Out: 12:00 PM
  • Cancelation: Please visit our website or contact us for detailed information about our cancellation policy.
  • Minimum Stay: 1 day, excluding holidays and over a Sat. in-season.