Great Oak Manor Bed & Breakfast on the Chesapeake Bay

10568 Cliff Road, Chestertown, Maryland 21620
Innkeeper(s): Holly McKee

Caulk (pet friendly)

$199.00 / $299.00 night

Like all the rooms at Great Oak Manor, this room’s name was born out of history; it was named for the Caulk battlefield and the only battle fought on Maryland’s Eastern Shore in the War of 1812.

The water calls you from your own private lookout of the Chesapeake Bay. Enjoy this spacious room with a luxurious king-size bed and a private bath that boasts walls the color of the sunsets, an inviting, rich red. Situated on the corner of the house on the second floor, the Caulk has an open feel and ample natural lighting from the waterfront windows.

The Caulk features its own heating/cooling unit.

It is one of three rooms that is Pet Friendly.

***During our peak season (mid April – October 31) we do require a 2 night minimum on weekends, and some holidays have a 3 night minimum.***

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D'Oench

$209.00 / $329.00 night

With a name from the first owner of the house, Russell D’Oench, you should expect nothing less than luxury. D’Oench had the original house built as his 26-room private residence, and his namesake holds nothing back.

Handsome finishes, such as crown molding and a grand fireplace, complement the panoramic views of the Chesapeake Bay. Being in the middle on the second means the D’Oench possesses some of the most stunning en-suite views of the Bay.

With a king-size bed, reading chairs, a gracious bath, and a working fireplace for the fall/winter season, it’ll be hard to leave your room. Stay for a night. Or two. Or three.

The D’Oench features its own heating/cooling unit.

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Geddes-Piper

$159.00 / $229.00 night

There’s something about this room that makes you feel right at home.

Nestled away on the third floor, this intimate room boasts an interior balcony where you can watch the boats go by on the Chesapeake Bay or spy Bald Eagles as they hunt for their prey. On the wall, there is a fine collection of black and whites from photographer, Marion E. Warren.

The room’s name stems from local merchants William Geddes and James Piper, names who are directly associated with the Geddes-Piper House in Chestertown. It’s widely believed that Piper bought the lot from Geddes and is the probable builder of the Geddes-Piper house that remains today.

The Geddes-Piper room hosts a king-size bed, private bath, and has it’s own heating/cooling.

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Hodges

$159.00 / $229.00 night

Experience the manor’s wilder side with natural views of squirrels chasing, bald eagles soaring, and red foxes running. The king-size bed befits a room this stunning with floral walls, a gorgeous fireplace, a private bath, and cozy chairs for reading. This room has a great view of the boxwood garden.

***During our peak season (mid April – October 31) we do require a 2 night minimum on weekends, and some holidays have a 3 night minimum.***

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Hynson

$139.00 / $199.00 night

The Hynson possesses the charm of a French country cottage, with the comforts of an estate home in Provence.

Look out a dormer window to find inspiring views of the water and the grounds of the estate. Located on the third floor, you’ll have a sweeping view of the property that is worth the trek up the stairs. The Hynson also features a beautifully decorated built-in bookcase and an inviting reading chair.

Retire to your room to enjoy the comforts of a king-sized bed with private bath and a heating/cooling unit.

***During our peak season (mid April – October 31) we do require a 2 night minimum on weekends, and some holidays have a 3 night minimum.***

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Marmaduke

$209.00 / $329.00 night

Rise to breathtaking views of the Chesapeake Bay from a king-size bed that begs you to stay under the covers for a moment longer.

Bright and airy, the Marmaduke features rich floral hues and is perfect for just gazing out at the view. With a cozy fireplace, walk-in closet and sumptuous bath, this luxury guest room is as lovely as the first land owner for which it is named.

Being on the corner of the house affords the room ample space and natural lighting, also making this room perfect to act as our bridal/honeymoon suite for couples hosting their wedding at Great Oak Manor, or sharing a romantic getaway together.

The Marmaduke has its own heating/cooling.

***During our peak season (mid April – October 31) we do require a 2 night minimum on weekends, and some holidays have a 3 night minimum.***

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Ringgold

$139.00 / $199.00 night

Comfort knows no boundaries in the graceful Ringgold room, which possesses a king-size bed, private bath, and cottage-style comfort. Blue gingham and French toile complement the white wainscoting. .

The Ringgold truly feels like your home by the sea – or in this case, the Bay. With an inviting reading chair plush with comfort and an expansive view from it’s third floor window of the front grounds and grand driveway.

Ringgold also boats a heating/cooling unit.

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Roese (pet friendly)

$179.00 / $269.00 night

Named for a former owner’s mother, Helen, the Roese suite looks out over the courtyard and carriage house. A stately bedroom with a king-size bed, and spacious bath with skylight, this Roese bears no thorns. The suite also has a separate sitting area with an electric fireplace that makes any chilly night cozier.

Conveniently located near the Conservatory, this suite serves as one of our three dog-friendly rooms and is also ideal for guests traveling as a family as there is ample space.

The Roese suite has central heating/cooling for your pleasure.

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Russell

$179.00 / $269.00 night

Named for Great Oak Manor’s most notable gamer, Frank Russell, the Russell Suite boasts a plush lounge area, a king-size bed, a fireplace, cathedral ceilings, and a large bath.

Situated on the third floor, this room maintains the aura of the notorious illegal gambling that used to occur in the room when Great Oak Manor was an elite Countrymen’s Club.

This majestic room has an old boy’s club feel with a softer side. Rich reds, plaids, and mahogany walls are downplayed by the oriental rugs, crisp linens, and Ralph Lauren curtains. The room is also home to a 55″ Flat screen HD TV. Let the games begin.

***During our peak season (mid April – October 31) we do require a 2 night minimum on weekends, and some holidays have a 3 night minimum.***

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Sterling (pet friendly)

$179.00 / $269.00 night

Named for Great Oak Manor’s most notable gamer, Frank Russell, the Russell Suite boasts a plush lounge area, a king-size bed, a fireplace, cathedral ceilings, and a large bath.

Situated on the third floor, this room maintains the aura of the notorious illegal gambling that used to occur in the room when Great Oak Manor was an elite Countrymen’s Club.

This majestic room has an old boy’s club feel with a softer side. Rich reds, plaids, and mahogany walls are downplayed by the oriental rugs, crisp linens, and Ralph Lauren curtains. The room is also home to a 55″ Flat screen HD TV. Let the games begin.

***During our peak season (mid April – October 31) we do require a 2 night minimum on weekends, and some holidays have a 3 night minimum.***

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Tylden

$229.00 / $299.00 night

With an Oriental Mural, think of it as Georgian meets Asian fusion.

The king-size bed is the perfect place to curl up and read a book as you gaze out at the Bay. A small iron balcony outside the door provides a serene spot to watch the sun set over the water, or to just gaze out and watch the squirrels and boats. Tylden features a stand-alone shower in its private bath.

***During our peak season (mid April – October 31) we do require a 2 night minimum on weekends, and some holidays have a 3 night minimum.***

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Wickes

$199.00 / $299.00 night

Rekindle a romance in front of a roaring fireplace in a room that overlooks the grounds of our magnificent estate.

Named for Captain Lambert Wickes, skipper of the 16-gun sloop that carried Benjamin Franklin to France, this room features a king-size bed, a walk-in closet, and a large, private bath. Crown molding and chair rails, built-in bookcases, reading chairs, and paintings of sailboats add just the right finishing touch.

***During our peak season (mid April – October 31) we do require a 2 night minimum on weekends, and some holidays have a 3 night minimum.***

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The Carraige House

$299.00 / $499.00 night

The Carriage House at Great Oak Manor is our newest accommodation. It boasts majestic views of the Eastern Shore with room for up to 6 people.

The Carriage House has a full service kitchen equipped for all of your cooking needs. The master is the King bedroom. In the loft area you will find a Queen bed. The Loft area also features a Queen and a twin Fold out for extra guests.

Sleeps 6

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  • Amenities

    Amenities

    At Great Oak Manor, our inn on Maryland’s Eastern Shore, 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.

    In suite we offer:

    • 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
    • All Comphy bed linens
    • Robes
    • 6 guest rooms have fireplaces (fireplace season is from November 1-April 1)

    Amenities for Outside:

    • Cruiser Bicycles
    • Kayaks
    • Canoe
    • Paddle Boards
    • Waterside firepit
    • Patio firepit
    • Private Chesapeake Bay beach access
    • Cornhole
    • A few extra binoculars for bird watching
    • Use of the amenities offered from the marina next door:
      • Pool
      • Fitness Room
      • 9-Hole Golf Course (bring your own gear)
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