The glorious Chesapeake Bay is the setting for a jewel of a Maryland Bed and Breakfast, Great Oak Manor. Waterside, Waterviews and water sports steep this elegant Georgian building in the sparkle and excitement of one of the great bays of the United States. 12 acres of beautiful property, including a walled garden leading to the private beach, surround this 12,000 square foot building from 1938.

Feel free to balance out leisure and exercise, whether you are using the Manor’s loaner bicycles, waterboards or kayaks, or lazing in front of the fire pit in an Adirondack chair or a hammock. Guests have free use of the adjacent complex that includes a swimming pool, fitness center and 9-hole golf course. You may not want to leave the Great Oak Manor, but don’t miss the beauties of nearby Chestertown, Maryland.

Chesapeake Bay

Get out the crab hammer, as seafood restaurants proliferate as well as other ethnic choices, including Italian, soups and salads and other options. For shopping, try unique stores such as Twigs & Teacups, Bookplate and Chester River Wine & Cheese await, as well as antique stores and galleries. For history and theatre, the area is not lacking in excellent options, including music in the park and by the river. The Chesapeake Wine Trail awaits, as do seasonal festivals such as the Chestertown Tea Party Festival, “Pirates and Wenches”, and Sultana Downrigging, which honors slips and schooners, and, for the holiday season, the Dickens of a Christmas Victorian Holiday Festival.

Pet-Friendly B&B on the Bay

A “Select Registry” member since 2003, Great Oak Manor is ready to provide comfort and elegance in one of 12 rooms with one family-extended size suite, 3 of which are pet friendly rooms. Lizzie the Manor Dog sends each pet visitor a welcome note with a gift package of bowls, blanket, toys and treats. Staff can direct you to restaurants in town that have pet-friendly patios, as well.

The rooms are decorated appropriate to the Georgian period of the Inn, with luscious rugs and antique decor. Many of the rooms feature balconies, fireplaces, clawfoot tubs, and most of the bathrooms are lit naturally, with skylights. The Carriage House is the family sized room, and other bedrooms include the Sterling, the Roese, and the Geddes-Piper, named for figures who were important to the Inn’s history.

Innkeeper Holly McKee is ready to greet you with drinks in the music room, recommend a book in the 850-volume library or direct you to great options for entertainment and relaxation. The breakfast is rich and appetizing, served in spacious common rooms, or, in good weather, on the porch.

Chesapeake Bay, Maryland Weddings

Chesapeake Bay weddings, elopements and corporate retreats are a specialty of the Manor, and can provide a memorable ceremony location for small and large weddings. Many companies choose the Manor for board retreats, some lasting several days and including overnight stays. Tesla is just one of the companies that has met at Great Oak Manor, which also offers not one, but two Tesla superchargers in their parking lot, truly 21st century convenience in an historic setting.

Considering that, as a private home, the Manor hosted the likes of John F. Kennedy, Ernest Hemingway and Guy Lombardo, among other luminaries, you are following excellent advice to choose Great Oak Manor on Maryland’s Eastern Shore.

More Info: Great Oak Manor | Maryland Bed and Breakfast | Book Direct


Great Oak Manor is a member of the bnbfinder Diamond Collection and accepts bnbfinder bed and breakfast Gift Cards. The bnbfinder Diamond Collection is an exclusive group of professionally inspected and/or highly rated luxury bed and breakfasts and inns. Each member of the bnbfinder Diamond Collection is required to have passed a professional inspection from a third-party industry-recognized inspection agency or achieved a high traveler review rating consecutively for each of the past three years.

 Members of this program offer guests exceptional experiences and levels of service in line with today’s discerning travelers’ highest expectations. bnbfinder invites you to peruse each of our Diamond Collection members. Remember to be sure and tell the innkeeper you found them via the bnbfinder Diamond Collection!

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