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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 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:
April 28, 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 Chesapeake Bay

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 Island Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
Floor Area:
  • 1200 sq. ft.
House Rules:
  • Max. occupancy: 6
  • non smoking only
  • pets considered ...
  • Events Allowed
  • children welcome
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.


Good! 3.9/5 -
(9 traveler reviews)

Waterfront Tilghman Island Cottage
average rating of 3.8888888 based on 9 reviews

Cozy and relaxing

  • 5 of 5

If you are looking for a place to curl up and read a good book or sit on the screened in porch and watch the passing boats, you will love this cute cottage. I brought a crockpot but other than that everything you need is provided and the owner is available but respectful of your privacy. I will be going back.


Fairfax, VA

  • Submitted: Sep 30, 2016
  • Stayed: Sep 2016
  • Source: HomeAway
Owner's Response: Thank you for your kind review. We are very happy that you enjoyed your stay. We look forward to hearing from you in the future.
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1 0
Pittsburgh PA


  • 2 of 5

Stayed here five times over last few years. Loved sitting on screened porch in afternoon. This year every weekday a wholesale seafood truck came at 11:00 AM and sat on the dock for three and a half hours with the truck running next to the house waiting for the fisherman to bring in their fish, it was very noisy. The beautiful view from the porch is partially blocked by the large shrubs. Owner went from whole house AC to separate units. We will not be coming back again.

  • Submitted: Sep 19, 2016
  • Stayed: Sep 2016
  • Source: VRBO, from HomeAway
Owner's Response: We're sorry that you did not enjoy your stay with us this year. I will make a note to cut back the shrubs for a better view.
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1 1

Comfort and Quaint

  • 4 of 5

This place was great for our Friends' Getaway. The view of the waterfront is fantastic and the pier was amazing for fishing and crabbing. The location was a short drive from St. Michaels, which made it very accessible for night activities. The screened in porch was perfect for us and the dogs. Everybody had an awesome time!

  • Submitted: Aug 1, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for your kind review. We are so happy that had an enjoyable and relaxing time. I hope that you will return in the future.
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1 0

Just the right place to "do nothing!"

  • 4 of 5

Intrigued by the idea that we could get away from the hustle and bustle just a short drive from home, I was looking for a place "to do nothing," that was on the water, and where we could bring our dog. (And, honestly, being affordable was also a criteria.) After checking out numerous places on Tilghman Island and close by, Captain's Watch was my choice!

My husband (who had no idea about this!) and I were quite happy with this choice! It is the place to "do nothing" .... we spent the majority of the time relaxing on the porch, reading, resting, watching the boats pass by. We lacked for nothing, and the owners were quickly responsive to questions prior to and once during our stay. It's a cozy, easy-going place.

We've mentioned it to friends and plan to return in the fall!

P.S. We did clean the grill before using it (looked as if it hadn't been done in awhile) and thought the porch could use a little TLC (perhaps just a little cleaning would help.) Still happy to be there!

  • Submitted: Jul 10, 2016
  • Stayed: Jun 2016
  • Source: HomeAway
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0 0


  • 3 of 5

When I choose this location I saw beautiful water front picture on the website.

Because I really like fishing. So I had big dream but I can't do fishing. That water just for boat passing way.

My dream was gone but my family has good time all day long in the house.

So overall wasn't that bed.

  • Submitted: Jul 5, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for your review. I'm sorry that you did not catch any fish of the dock. I suppose that is why they call it fishing and not catching. That is half the fun, right? If you return in the future I suggest that you try a local fishing charter. They're lots of fun and the captains are good about taking you to where the fish are.
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0 1

Great getaway

  • 5 of 5

This place is great for watching the water and relaxing.

  • Submitted: Nov 2, 2015
  • Stayed: Oct 2015
  • Source: VRBO, from HomeAway
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0 0


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

Tilghman Island Cottage Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
My Standard Rate
2 night minimum stay

Additional information about rental rates

Pet Fee $50
Refundable damage deposit $50
Tax Rate 10.0%

Owner's Cancellation Policy

100% refund if canceled at least 30 days before arrival date.
Enter dates for accurate pricing
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