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HomeAway Inc.

Private Eastern Shore Retreat

#397938 · Vacation rental in , MD,

7 Bedrooms
13 guests
5 Full Bathrooms
Vacation rental

Property Description

Bowlingly Estate was built in 1733 and is one of the oldest dated constructions on the central Eastern Shore. It sits on 10 manicured grassy acres with stunning views of the Bay and even more amazing sunset views.

The house does have historic significance as well. According to the contemporary account of a local militia officer, Major Thomas Emory--the home was ransacked by the British during the War of 1812. At dawn on August 13, 1813, a flotilla of English ships landed at Bowlingly's wharf. The British troops severely damaged the house, tearing out staircases, ripping wallpaper, and stealing valuables, before encountering the local militia. Rumor has it there are still canon balls in the walls.

There have been multiple additions and renovations of the home over the years and currently the home is about 10,000 square feet with multiple outbuildings and a large pool.

Our home has 5 bedrooms on the second floor with two master suites (one with a queen bed and the other with a king), three additional bedrooms on the same level (one with an en suite bath and the other share a bath) The third floor has one private queen bedroom, an alcove with a single bed and a large open carpeted space beyond.

As you enter the home you see the Chester River through the door to what was traditionally the front of the house as it faced the water. The entryway is graced with a beautiful antler staircase with antique wallpaper all the way up to the second floor.There is a wonderful cozy library with gas fireplace for cool evenings to the left as you enter the home. As you continue your journey you will pass a very large half bath and then make it into the great room with fantastic natural light again with breathtaking views of the water. The sun room sits just a few steps toward the water and is currently used as a playroom large comfy armchairs for relaxing.

The kitchen is next to the great room with a large island, dishwasher, viking fridge and ovens and a 5 Star commercial range. Kitchen is fully stocked with plates, pots, pans,etc...

The washer and dryer are just beyond the kitchen as is the breakfast room and dining room.

Outside you will find 10 manicured acres with a playground for children, large pool, relaxing hammock and of course amazing water views. Next to the dock you will find a small sandy beach where it is easy to launch one of our three kayaks for a peaceful paddle around Queenstown Creek.

Close to Queenstown Premium Outlets, restaurants in Kent Narrows, and only 25 minutes to Easton. Large Safeway grocery store about a 10 min drive.

Weddings or other events will be considered but additional fees apply.

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House Rules

Check In Time: 16:00
Check Out Time: 11:00
Max occupancy: 13 guests

Sleeping Arrangements

Common Space
Bed types not specified
Bedroom 1
Bed types not specified
Bedroom 2
Bed types not specified
Bedroom 3
Bed types not specified
Bedroom 4
Bed types not specified
Bedroom 5
Bed types not specified
Bedroom 6
Bed types not specified
Bedroom 7
Bed types not specified


Rate Name Nightly Weekend Weekly Monthly
Default Rate
2 Nights Minimum
$1277 CAD - - -
01/01/18 - 03/31/18
2 Nights Minimum
$1675 CAD - - -
04/01/18 - 06/08/18
2 Nights Minimum
$2836 CAD - - -
06/09/18 - 09/15/18
2 Nights Minimum
$3352 CAD - - -





Restaurant On Site
Guided Fishing Tours

Availability Calendar


  • Unavailable
  • Check In Available
  • Check Out Available
Availability last updated Mar 16, 2018
Overall Rating

Owner Information