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Tilghman Island - Spectacular Sunsets Over Chesapeake Bay

(3 Reviews)

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Last updated: 03/27/2017
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:2 nights
  • Sleeps:5
  • Bedrooms:3
  • Bathrooms:2
  • Property type:Cottage
  • Internet:Yes
  • Pets considered:Ask Owner
  • Wheel chair accessible:N/A

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
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Member since: 2008

Speaks: french
Response time: Within 24 hours
Response Rate: 100%
Calendar last updated: 03/27/2017

Property Type

  • Cottage
  • 1350 sq. ft.

House Rules

  • Max. occupancy 5
  • Non Smoking Only

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals


Bedrooms: 3 Bedrooms, Sleeps 5, Beds for 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...moreless

Bathrooms: 2 Bathrooms

Other Amenities

  • 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....moreless


  • CD Player
  • DVD Player
  • Music Library:

    Satellite Radio...moreless

  • Satellite / Cable
  • Stereo
  • Television
  • VCR
  • Video Library


  • Adventure
  • Away From It All
  • Budget
  • Historic
  • Romantic
  • Sports & Activities


  • Festivals
  • Health/Beauty Spa
  • Marina
  • Museums
  • Playground
  • Restaurants
  • Winery Tours

Local Services & Businesses

  • Groceries

Leisure Activities

  • Antiquing
  • Bird Watching
  • Boating
  • Eco Tourism
  • Horseback Riding
  • Shelling
  • Shopping
  • Sight Seeing
  • Walking
  • Wildlife Viewing

Location Type

  • Beach View:

    All cottages are on the Chesapeake Bay...moreless

  • Waterfront:

    180 degree views of the Chesapeake Bay with 3 docks for shared use and 4-season Crab Shack out by water with wood-burning fireplace and TV....moreless

Sports & Adventure Activities

  • Basketball Court
  • Cycling
  • Deepsea Fishing
  • Fishing
  • Golf
  • Hiking
  • Jet Skiing
  • Kayaking
  • Mountain Biking
  • Pier Fishing
  • Sailing
  • Swimming
  • Wind-Surfing


  • Dining Area
  • Seating for 4 people


  • Air Conditioning:

    Portable and window air conditioners available...moreless

  • Hair Dryer
  • Iron & Board
  • Linens Provided:

    For an additional charge...moreless

  • Living Room
  • Parking
  • Towels Provided:

    for a additional charge...moreless

  • Wireless Internet


  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Kitchen:

    Fully equipped kitchen...moreless

  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster


  • Deck / Patio
  • Gazebo:

    We have a shared crab shack for crab feast parties. For an additional charge we will host the crab feast....moreless

  • Outdoor Grill


Write a review 5
from 3 traveler reviews
Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
My Standard Rate
2 night min stay

Additional information about rental rates


  • Refundable Damage Deposit $250
  • Linen Service $50
  • Pet Fee $50
  • Tax Rate 4%

Owner's cancellation policy:

Policy available by contacting owner when booking

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Last updated: 03/27/2017
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates


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.


Owner info

Year Purchased: 1996

About the owner: 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.

Why the Owner Chose Tilghman Island, MD, USA:
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.

The Unique Benefits at this Cottage:
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.

Contact us

Speaks: french
Response time: Within 24 hours
Response Rate: 100%
Calendar last updated: 03/27/2017

Send email



  • Yellow cottage

    Yellow cottage

  • Kitchen in Yellow Cottage

    Kitchen in Yellow Cottage

  • Yellow Cottage

    Yellow Cottage

  • Sunset at Tilghman Landing

    Sunset at Tilghman Landing

  • White Cottage

    White Cottage

  • Kitchen - White Cottage

    Kitchen - White Cottage

  • White House - Bedroom 2

    White House - Bedroom 2

  • Crab Shack Party

    Crab Shack Party

  • Capt. Jeff - at sunset

    Capt. Jeff - at sunset

  • Pergola at sunset - with privacy drapes

    Pergola at sunset - with privacy drapes

  • New Cottage - 3 bedrooms

    New Cottage - 3 bedrooms

  • Bedroom in Yellow Cottage

    Bedroom in Yellow Cottage

  • Shared Dock

    Shared Dock

  • White Cottage, Grey Cottage and Yellow Cottage

    White Cottage, Grey Cottage and Yellow Cottage

  • Eagles nest

    Eagles nest

  • View from White Cottage - overlooking Crab Shack, Yellow Cottage and Pergola

    View from White Cottage - overlooking Crab Shack, Yellow Cottage and Pergola

  • Bedroom 1 - White Cottage

    Bedroom 1 - White Cottage

  • Shared Crab Shack with Wood-burning fireplace and TV

    Shared Crab Shack with Wood-burning fireplace and TV

  • Crabbing on the Bay - Sook

    Crabbing on the Bay - Sook

  • Blue Heron on boat dock

    Blue Heron on boat dock

VRBO #192419

This listing was first published here in 2008.

Date last modified - Monday, March 27, 2017

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