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

Tilghman Island - Spectacular Sunsets over Chesapeake Bay

Bedrooms 3
Space 1,350 sq. ft.
Property type cottage
Minimum Stay 2 nights


About the property

Waterfront Cottage with Private Dock, 3 Bedroom, 2 Bath

Located on the Chesapeake Bay side of Tilghman Island, this beautiful two-story, two bedroom cottage is available for rent throughout the year. Our cottages have stunning views of the bay from the second floor bedrooms - and private balcony and/or deck. There are hardwood floors throughout, a full service kitchen with dishwasher and microwave and outdoor gas grill. Enjoy the use of the 3 shared docks, crab traps, the Crab Shack (with wood burning stove, small drink fridge, CD player/radio and DVD player) and a Pergola with seating for 4. The dazzling sunsets over the Bay are extraordinary as though they were choreographed just for us. The chatty waterfoul are fascinating to watch and we get daily visits from a wide array of birds, migrating geese, ducks (and ducklings), osprey and the occasional bald eagle. This is the perfect romantic getaway. An extensive bike trail (the new Michener Byway) extends from Tilghman to St. Michaels and out to Oxford via the Belleview/Oxford Ferry. We are minutes (walking distance) from world class restaurants, kayaking, fishing, skipjack tours, historic St. Michaels, and Antique Shops.

Keywords: Tilghman Island, Cottage, Chesapeake Bay, Waterfront

More Details

Jacque and Patrick
Member since: 2008
Speaks: french
Response time:
Within 12 hours
Response rate:
Calendar last updated:
December 19, 2017

About Jacque and Patrick

We arrived in Tilghman Island in 1996 in search of a watermen community much like that of Half Moon Bay (CA) from where we came. We have spent the last 15+ years developing Tilghman Landing into a Chesapeake Bay retreat that we love to share. In addition to building our waterfront cottages, we spend our time fishing, crabbing, boating and enjoying the beauty of our Bay-side retreat. Our cottages are open and airy – with ceiling fans throughout and a nice almost constant breeze blowing across the Bay. We have a hammock and beach chairs available for watching the evening sunset. The property is private, quiet and perfect for a romantic getaway or family get together.

Jacque and Patrick purchased this cottage in 1996

Why Jacque and Patrick chose Tilghman

Tilghman Island is the East Coast version of Half Moon Bay, California with its colorful history, abundant seafood throughout the seasons (fish, crabs and oysters), maritime activities (boating, kayaking, fishing, jet skiing) and California Sunsets over the Bay. We are also about a mile from Poplar Island (directly off our pier) where a successful restoration effort led by the U.S. Army Corps of Engineers has returned the island to 1,140 acres. When work on Poplar Island is complete the island will be a maze of smaller islands, ponds, channels and marshes. Ospreys, egrets, terns, herons, eagles, double-breasted cormorants, black ducks and other wild fowl have already discovered an enlarged Poplar Island – a true bird-watching opportunity. We are located about 2 hours from Baltimore, Washington DC and Philadelphia, PA. Our guests come from all over the world to experience all that the Chesapeake Bay has to offer.

What makes this cottage unique

Our cottage is very private at the end of a quiet dead-end road. Our guests often set up bocce ball and volleyball nets and we have a horseshoe pit for some friendly competition. On Saturday night, depending upon the season, we will often cater a Crab or Oyster Feast in the Crab Shack for our guests who want this Maryland Eastern Shore experience. There are year-round festivals and holiday events, an extensive bike trail, world class restaurants, shopping and cultural centers – Tilghman Watermen Museum, Philips Wharf Environmental Center and St. Michael’s Maritime Museum. The Lady Patty, one of the last remaining sailing skipjacks is available for a sunset or daytime sail – within walking distance of our cottages. We have 3 docks that are perfect for sunbathing, crabbing, fishing or just enjoying a glass of wine while watching the amazing sunset. We live on the property and are therefore available to assist with special requests.


Tilghman Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
Floor Area:
  • 1350 sq. ft.
House Rules:
  • Check-in: Flexible
  • /
  • Check-out: Flexible
  • Max. occupancy: 5
  • Max. adults: 4
  • Parties/events not allowed
  • Pets considered ...
  • Non smoking only
  • We do NOT allow ONLINE booking for our property without communication with us first - we NOT honor a reservation made without our direct knowledge.
Location Type:
  • Beach View ...
  • Beachfront ...
  • Waterfront ...
  • Adventure
  • Away From It All
  • Budget
  • Historic
  • Romantic
  • Sports & Activities
  • Air Conditioning ...
  • Hair Dryer
  • Iron & Board
  • Linens Provided ...
  • Living Room
  • Parking
  • Towels Provided ...
  • Wireless Internet
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • seating for 4 people
  • 2 Bathrooms
  • Bathroom 2 - toilet , combination tub/shower
    Bathroom 1 - toilet , shower
  • 3 Bedrooms, Sleeps 5
  • Bedroom 4 - 1 twin/ single
    Bedroom 1 - 1 queen
    Bedroom 2 - 2 twin/ single
  • Queen size Bed, Single with Trundle, Single 2 Full Bathrooms, One with Tub Linens provided at additional charge
  • CD Player
  • DVD Player
  • Music Library ...
  • Satellite / Cable
  • Stereo
  • Television
  • VCR
  • Video Library
  • Deck / Patio
  • Gazebo ...
  • Outdoor Grill
  • festivals
  • health/beauty spa
  • marina
  • museums
  • playground
  • restaurants
  • winery tours
Leisure Activities:
  • antiquing
  • bird watching
  • boating
  • eco tourism
  • horseback riding
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • groceries
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • hiking
  • jet skiing
  • kayaking
  • mountain biking
  • pier fishing
  • sailing
  • swimming
  • wind-surfing
Shared use of 3 piers and 'Crab Shack' for Crab Feast parties. Crab Shack has small fridge for drinks, DVD player and wood burning fireplace. We often host crab feast parties - purchase, cook and serve the crabs (add'l cost). Hammock and beach chairs available on the property to relax and watch the sunset. A cozy pergola with seating fo 4 is great to watch the dazzling sunsets. There are also bikes available for use on the island.


5/5 -
(3 traveler reviews)

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Tilghman Island - Spectacular Sunsets over Chesapeake Bay
average rating of 5.0 based on 3 reviews


  • 5 of 5

We chose to come to Maryland from Ohio on a whim for an elopement. We wanted a quiet and beautiful place on the bay and we lucked out finding this gem! We stayed in the Jelly Fish House, it is brand new and gorgeous, just what you would imagine for a beach house. We spent a lot of time relaxing on the dock and in the hammock looking at the beautiful views and sunsets. My three boys had a ball fishing, jumping in the water from the dock and catching blue crabs-we had never seen those before!! We definitely had three teary-eyed boys when it was time to leave. We had a magical weekend! We wouldn't have changed a thing and would love to come back. Jacque and Patrick were fantastic!

  • Submitted: Aug 19, 2016
  • Stayed: August 2016
  • Source: VRBO, from HomeAway
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1 0
Freeport, PA

Beautiful & Serene

  • 5 of 5

Our stay was absolutely wonderful!!! If relaxing, peace and quiet with fishing & crabbing is what you are looking for then this is the place for you! Private property at the end of the road! No neighbors around! Breathtaking views and sunsets!!! Great fishing!! The cottage was beautiful!! The colors are so homey that it instantly feels like home. Beautiful views from the deck! Buy some wine from the local stores and enjoy it on the deck. The crab shack would be a great place to gather. Unfortunately our trip was too short and the weather didn't cooperate so we weren't able to take advantage of it....this time. The owners were absolutely fantastic with any questions and so helpful with suggestions of where to eat, shop and buy seafood!!! We are already talking about when we can go back again!

  • Submitted: Sep 24, 2013
  • Stayed: September 2013
  • Source: VRBO, from HomeAway
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1 0
United States

Great Weekend

  • 5 of 5

My boyfriend and I were in search of a quiet place to escape the hustle of DC for Memorial Day. Realizing it would be our first vacation together, we decided to try Tilghman Landing because of its waterfront views and welcoming descriptions.

After 3 days of a perfect vacation, we didn't want to leave. The amenities are more than what you expect and both Jacque and Patrick are exceptionally friendly and welcoming people. They went through the trouble of setting up a crab dinner on Saturday night for us and a few other folks--it was a night to remember with great company.

Overall, would highly suggest to anyone to schedule a stay and be prepared for a great visit!

  • Submitted: May 28, 2013
  • Stayed: May 2013
  • Source: VRBO, from HomeAway
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3 0


Our property overlooks the Poplar Island Bird Sanctuary which is being preserved and developed by the Government. We have hundreds of species of all types of birds including Bald Eagles, Osprey, Herons, and many more. We are walking distance to several marinas where you can rent kayaks, jet skis and fishing trips. We are also walking distance to Philips Wharf Environmental Center and voyages on The Lady Patty - one of the last sailing Skipjacks in the world.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Pet Fee $50
Damage Deposit $250

Owner's Cancellation Policy

  • 50% refund if canceled at least 7 days before arrival date.
  • 100% refund if canceled at least 14 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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