Captain's Watch Cottage, located on Tilghman Island on the Eastern Shore of the Chesapeake Bay, is the perfect place to get away from it all!

Call Kelley Cox


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Roll over photo to see other views from Captains Watch and the area.

Captain's Watch is a Waterfront Cottage which has a screened porch with beautiful sunrise view of Knapps Narrows. It is nestled in a Working Watermens Village, 12 miles from Historic St. Michaels, Maryland on the Eastern Shore. The whole family will be entertained by the boating, kayaking, fishing and crabbing opportunities.
The Cottage has a dock, kayak launch and a Hot Tub for your relaxation. There are 4 Restaurants on the Island serving the Local Fare of Chesapeake Bay Seafood in many different ways. The Owners are on site and live next to the cottage. We have a Gas BBQ Grill for grilling your catch after a hard day of fishing. Captain's Watch has a full kitchen, washer/dryer, central AC, Cable TV, & VCR. Come to our shores and relax on the porch and watch the waterman toil at their labors of catching Chesapeake Bay Seafood and savor the flavor of the Land of Pleasant living. The Master Bedroom has a queen size bed, the guest bedroom has a trundle bed that can be made as 2 twins or a King, and the Living Room has a queen size sleep sofa.


• Kayak Launch
• Cable TV
• Central AC
• BBQ Grill
• Fishing Dock
• Hot Tub
• Washer Dryer
• Full Kitchen


Bedroom(s): 2
Bathroom(s): 1
Sleeps: 6
Lot/Acres: 35352 Sq Ft
Sq.Footage: 1008
Handicap Access: No
Smoking: No
Pets: Yes

Chesapeake Bay Maritime Museum in St. Michaels
A Variety of Boat and Kayak Tours in season.
Boat and personal watercraft rentals available
Shopping in the Quaint town of St. Michaels
Relaxation at a slower pace.

Your hosts, Kelley and Jerry Cox are also the owners of Dockside Express Ltd. Cruises and Tours. Be sure to ask about events available during your stay. You can find out more at

Price information:
Weekday: $125.00 per night in season
Weekend: $175.00 per night in season

Off Season Rates from December 15 - March 15:
$75.00 per night
2 night minimum

To inquire about availabilty of specific dates, check here at Webervations.

Other costs:
Pet fee is $50.00 per Stay

50% Deposit required with returned contract to hold the reservation.
Security Deposit to be held on a Credit Card

Cancellations or Refunds:
Cancellation must be made not less than 30 days in advance for a full refund less the $50.00 processing fee.
Partial refunds less than 30 days notice if space is resold

  Customers keep coming back to savor the view and drain their stress away