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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Waterfront Tilghman Island Cottage ***Newly Redecorated***

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 a beautiful sunrise view of Knapps Narrows. It is nestled in a working watermen's 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.

Outside around the property:

The Cottage has a kayak launch and a hot tub (seasonal) for your relaxation. There is a place to rent kayaks just down the road. We do have a dock that it is possible for your to fish or crab off of but we ask that you be respectful of the seafood buyer and watermen that unload their catch on our dock. In the yard you can sit back in one of our Adirondack chairs and sip an ice cold drink or maybe enjoy some crabs while sitting at our picnic table.

Screened in Porch:

This is a rural area and we do have bugs. Not an over abundance but around dusk the mosquitoes can get pesky. There's no better way to still be able to sit outside and enjoy the views but without getting eaten up than sitting on our screened in porch. On the porch we also have an electric BBQ Grill for grilling your catch after a hard day of fishing.

Living Room:

When you walk into the cottage from the porch you arrive in the living room. In 2017 we redecorated most of the cottage and purchased new furniture. The living room has a very comfortable love seat and chair as well as a couch that can be folded out into a full/queen size bed. Mounted on the wall is a new flat screen TV with cable.


Captain's Watch has a full kitchen with just about anything you may need to cook or eat your meal...all you need to bring is your ingredients. A refrigerator, microwave, and an oven with a range are all ready for you to use. We do have a coffee maker but you will need to provide your own ground coffee and filters.

There is a table that can seat 6 people. Please make sure if you plan to cook that you bring all your ingredients. Sometimes departing guests leave condiments, spices, or other cooking stuff but it is not guaranteed to be present at the cottage when you are there.


Our master bedroom has a queen size bed and the second bedroom has a twin trundle bed that can be pulled out to make two twin size beds or one king size bed. Both bedrooms have dressers if you would like to unpack and put your things away. There are televisions located in both bedrooms as well. It is always nice to have the ability to wash your clothes and you will find a washer and a dryer in the master bedroom closet. Linens are provided.


In the bathroom you will find a bathtub with a shower and of course a toilet and sink. We provide toilet paper and bath towels but we do not provide shampoo or body wash.


Other amenities that Captain's Watch has to offer are Air Conditioning is those hot summer months and heat in those cold winter months! Did I mention Wifi? The cottage has free wireless internet for your use so if you need to get some work done while you are here or just want to scroll through facebook without using data we have you covered. In the unfortunate case that you need to work on your vacation there is a desk that you can make your office away from your office.

Come to our shores and relax on the porch and watch the watermen toil at their labors of catching Chesapeake Bay Seafood and savor the flavor of the Land of Pleasant living. The cottage is available year round and pet and kid friendly.

The Owners are on site and live next to the cottage.


Surrounding Area:

There are 2 Restaurants on the Island serving the local fare of Chesapeake Bay seafood in many different ways. We have a country store down the road about a mile where you can buy general items plus beer and wine or you can order takeout.

St. Michaels is a short drive away and there are many cute shops and wonderful restaurants to eat at. Also in St. Michaels there is a distillery, a winery, and a brewery. Take a walk around a discover the history of the "town that fooled the British"


Phillips Wharf Environmental Center- Estuarium/Aquaculture Tours- Tilghman

Fishing/crabbing charters-Tilghman

Chesapeake Bay Maritime Museum in St. Michaels

A Variety of Boat and Kayak Tours in season.

Boat and personal watercraft rentals available nearby

Shopping in the Quaint town of St. Michaels

Relaxation at a slower pace.

Keywords: Cottage

More Details

Kelley Cox
Member since: 2009
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
April 25, 2018

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. Kelley's niece Missy now helps run the cottage by taking care of the bookings and correspondence with guests. This is a family run cottage that is laid back and friendly. If you are looking for a place that will feel like a home away from home then our cottage is for you.

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 an electric 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
  • Romantic
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace ...
  • Heating ...
  • Internet ...
  • 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
  • seating for 6 people
  • 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
  • Books
  • DVD Player
  • Games
  • Satellite / Cable
  • Television ...
  • VCR
  • Video Library
  • Bicycles ...
  • Boat ...
  • Golf ...
  • Kayak / Canoe ...
  • Lanai / Gazebo ...
  • Lawn / Garden
  • Outdoor Grill ...
  • Tennis ...
  • 1 bicycles
  • Long-term Renters Welcome
  • alternative lifestyle
  • limited accessibility ...
Pool / Spa:
  • Hot Tub ...
  • churches
  • health/beauty spa
  • library
  • marina
  • museums
  • playground
  • restaurants
  • winery tours
  • zoo
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • photography
  • 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 -
(19 traveler reviews)

63% Complete
21% Complete
10% Complete
5% Complete
0% Complete
Waterfront Tilghman Island Cottage ***Newly Redecorated***
average rating of 4.4210525 based on 19 reviews

Good experience.

  • 5 of 5

There was plenty of room for the four of us.

All of the necessities were there for cooking the meals we took with us.

Never had a problem getting a response from Kelley when I had a question.

We would stay there again.

  • Submitted: Jan 27, 2018
  • Stayed: January 2018
  • Source: VRBO, from HomeAway
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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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1 0

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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1 0

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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2 0

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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1 0

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


Nearest Airport
75 Miles
Baltimore Washington International
Nearest Barpub
0.5 Miles
Character's Bridge Restaurant
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
Character's Bridge Restaurant
Nearest Beach
83 Miles
Ocean City
Car: necessary

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.




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.

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