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Waterfront Tilghman Island Cottage

Bedrooms 2
Space 1,200 sq. ft.
Property type cottage
Minimum Stay 2 nights


About the property

Cottage, 2 Bedrooms + Convertible bed(s), 1 Bath, (Sleeps 2-6)

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 kayak launch and a Hot Tub for your relaxation. There is a place to rent kayaks just down the road.

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, & DVD/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. The cottage is available year round and pet and kid friendly.



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.

Keywords: Cottage

More Details

Kelley Cox
Member since: 2009
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
December 15, 2017

About Kelley Cox

Your hosts, Kelley and Jerry Cox, each hold a 50-ton Captain’s license and have been involved in Chesapeake Bay research for a combined total of 55 years. Jerry grew up on a Tobacco farm across the Bay in Calvert County and worked as a research vessel Captain for the State of Maryland. Jerry’s roots are from nearby Hooper’s Island, where his great, great grandfather William Hooper was a schooner captain aboard the Florence Lee. Kelley’s ancestors have been in this area since the early 1600’s when Edward Comins and his wife Elizabeth served as indentured servants of William Claiborne on Kent Island. Her Grandfather, Russell Phillips, was one of President Harry Truman’s favorite fishing boat captains during his frequent retreats to the Eastern Shore. Kelley is a Biologist and the Executive Director of Phillips Wharf Environmental Center.

Kelley Cox purchased this cottage in 1995

Why Kelley Cox chose Tilghman

Kelley's parents built the cottage as a weekly vacation rental in the 1970's. Kelley & Jerry decided the added income would help out and started renting the cottage as a vacation rental about 6 years ago.

What makes this cottage unique

The property overlooks Knapps Narrows one of the busiest waterways on the East Coast you can relax on the porch and watch all the boats going by. We also have a commercial waterman using part of our dock so fresh seafood is available to our guests. Tilghman Island is a fishing village on the Chesapeake Bay so you can fish and crab off of our dock. We have a screened porch with a gas grill for cooking out and a hot tub to relax in after a taxing day of shopping in nearby St. Michaels. We have a park nearby for bird watching and exercising in and it has play equipment for the kids.


Tilghman Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
Floor Area:
  • 1200 sq. ft.
House Rules:
  • Max. occupancy: 6
  • pets considered ...
  • Events Allowed
  • children welcome
  • non smoking only
Location Type:
  • Village ...
  • Waterfront ...
  • Away From It All
  • Budget
  • Family
  • Historic
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace ...
  • Heating ...
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Parking
  • Parking Off Street
  • Parking for RV/Boat/Trailer
  • Telephone ...
  • Towels Provided
  • Washing Machine
  • Wireless Internet ...
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • 1 Bathroom
  • Bathroom 1 -
  • Bath tub/shower combo
  • 2 Bedrooms, Sleeps 6
  • Queen size Bed (1), Twin trundle bed which can make a King (1), Sleep Sofa - can be 2 twins or a King (1)
  • Books
  • DVD Player
  • Games
  • Satellite / Cable
  • Television
  • VCR
  • Video Library
  • Bicycles ...
  • Boat ...
  • Golf ...
  • Kayak / Canoe ...
  • Lanai / Gazebo ...
  • Lawn / Garden
  • Outdoor Grill ...
  • Tennis ...
  • Long-term Renters Welcome
  • alternative lifestyle
  • limited accessibility
Pool / Spa:
  • Communal Pool ...
  • Hot Tub
  • churches
  • health/beauty spa
  • library
  • marina
  • museums
  • playground
  • restaurants
  • winery tours
  • zoo
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • scenic drives
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • fly fishing
  • golf
  • hunting
  • ice skating
  • jet skiing
  • kayaking
  • pier fishing
  • sailing
  • sound/bay fishing
  • swimming
  • tennis
Trundle bed that makes 2 twins or a king bed. Electric Fireplace.


Excellent! 4.4/5 -
(18 traveler reviews)

61% Complete
22% Complete
11% Complete
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Waterfront Tilghman Island Cottage
average rating of 4.388889 based on 18 reviews

Restful and lovely

  • 4 of 5

I thoroughly enjoyed my time at Captain's Watch. The view from the screened porch is lovely and the surrounding residential area quiet. If you're looking for an affordable, restful spot on the water, this is it. Yes, it is next to commercial fishing activity, but I liked having that connection with the everyday reality of people's lives on the island. The cottage was well furnished and provided everything I wanted. The highlight of my trip was being able to see the sunrise from one side of the island and walk a short distance to the other side to see the sunset on the bay. How many places can you do that?

  • Submitted: Sep 11, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Relaxing Time Away

  • 5 of 5

We stayed at this property from Monday the 21st to Friday the 25th. It was quiet and comfortable. We enjoyed watching the crab boats selling their catch at the pier, watching the boats going by and I especially enjoyed sitting on the screened in porch at night listing to the crickets and the water lapping against the shoreline. As avid birdwatchers, we were especially delighted in the juvenile bald eagle who graced us with his presence each day in a nearby tree. Osprey were also a frequent guest as there was a nest very close to the shoreline. We had a very relaxing week tucked into our own little slice of paradise. We hope to be back again.

  • Submitted: Aug 29, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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peacefull cottage

  • 5 of 5

we had a great time . we caught the a lots of fish and crabs.

The cottage was very clean and very comfortable.

the owner was very nice. When i need a small question the owner coming very fast. We have nothing to complane.

We are very sure going again coming fall for fishing.

  • Submitted: Aug 15, 2017
  • Stayed: July 2017
  • Source: HomeAway
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Beautiful Property

  • 5 of 5

Had a great time! The water view was fantastic! Peaceful and you got to view the crab boats coming in to unload their catch. The owners live right in front but the only time we saw them is when we arrived and left. Would love to return again.

  • Submitted: Aug 9, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Graduation Surprise

  • 5 of 5

My family enjoyed our stay. Watching all different types of boats coming and going was nice. The family caught tons of fish. Watching the sunrise was amazing. We were lucky to be there to see a beautiful full moon over the water. The owners were very nice.

  • Submitted: Jun 13, 2017
  • Stayed: June 2017
  • Source: HomeAway
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2 0
Arlington VA

Urban Escape

  • 5 of 5

Closest you can get to the water without a boat! The very attentive owner, water views, and watching the boats go by make a stay in this recently redecorated cottage a special treat. This budget friendly bungalow with a screened in porch was perfect for our 3 day getaway. Good for restoring the batteries and experiencing life on a small, beautiful island. If you want to do some serious shopping, wine tasting or have a gourmet meal, St. Michaels is only about 12 miles away.

  • Submitted: Jun 2, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
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Nearest Airport
75 Miles
Baltimore Washington International
Nearest Barpub
1 Miles
Harrison's Blue Crab Deck Bar
Nearest Ferry
15 Miles
Oxford Bellevue Ferry
Nearest Golf
12 Miles
Harbourtowne Resort
Nearest Train
75 Miles
Baltimore Washington International
Nearest Motorway
23 Miles
Route 50
Nearest Restaurant
0.5 Miles
Characters at the Bridge
Nearest Beach
83 Miles
Ocean City
Car: recommended

We are on an Island that is 3 miles long and 1 mile wide.

Historically a fishing village, there are lots of ways to get out on the water here. We have 5 restaurants each with it's own specialties, but fresh seafood is a must here.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Pet Fee $50
Damage Deposit $50

Owner's Cancellation Policy

100% refund if canceled at least 30 days before arrival date.