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Eastern Shore Waterfront Estate, Private Beach, Deep Water

6 Reviews
Bedrooms 8
Half Baths1
Property type estate
Minimum Stay nights

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Half Baths
Minimum Stay


Trappe Estate Rental Photos and Description

8 Bedrooms - 6.5 Baths

Martins Point is a late 18th Century house and cottages on Maryland's historic Eastern Shore. It is located on a secluded finger of land, surrounded by water on three sides, a place to unwind, immerse yourself in the natural beauty of the Chesapeake Bay and reconnect with family and friends.

The house and cottages include 8 bedrooms and can accommodate 15+ guests. Furnishings reflect our family's taste: an appreciation of the farm's rural, colonial origins offset by a love of antiques and oriental rugs.

The pool and front lawn open on a favorite anchorage of Maryland sailors who frequently come and go during summer months. Great Blue Herons, bald eagles and ospreys drift by daily. Our dock can accommodate boats with up to 4 ft draft. The lagoon in front of the house, protected from weather on 4 sides will accommodate larger boats at anchor -- bottom is 12 feet.

  • children welcome
  • non smoking only
  • pets not allowed
  • wheelchair accessible

Tom Dann
Member since: 2008
Speaks: french
Response time:
Within a day
Response rate:
Calendar last updated:
August 1, 2016
Call Owner

About Tom Dann

Martins Point has been in our family for four generations. My grandfather acquired the place from the original colonial settlers, the Martin family, who received a Kings Grant in the 1600's and many of whom were laid to rest in the family graveyard located in our sheep pasture. There is much evidence of the aboriginal occupants of the land as we have found many arrowheads and stone axes. The farm was on the Underground Railroad before the Civil War, and archeologists excavated a dugout log canoe (now in the Frederick Douglas museum in Baltimore) thought to be used to secret fugitives across the Choptank on the road to freedom.

Tom Dann purchased this estate in 1939

Why Tom Dann chose Chesapeake Bay

The Eastern Shore is a very special place, and when our grandfather bought it in the 1930s there was no bridge and the area was so isolated that the locals spoke a dialect almost like Elizabethan English. Martins Point is close to all of the attractions of the area but is uniquely isolated with no houses in sight and water all around, more like being on an island.


based on 6 traveler reviews

Eastern Shore Waterfront Estate, Private Beach, Deep Water
average rating of 5.0 based on 6 reviews
Washington, DC

Great location for a big, family birthday celebration

  • 5 of 5

We gathered in June 2016 from all over -- CT, NJ, DC and PA at this wonderful estate -- to celebrate a milestone birthday. Everyone was comfortable in their rooms and the house has a warm/loving, family vibe. The second floor porch was perfect for the one night when we had a chance to watch a storm roll in. The property was perfect for everyone's diverse interests -- running/ walking, fishing, boating, and swimming in the pool. We rented the Dann's skiff and their two kayaks which were really fun (worth the extra, nominal cost). The kitchen is not huge, but somehow we all made it work and enjoyed cooking together. We would definitely rent this property again; our ages ranged from 55 to 9 and all said they'd like to return. The caretaker on the property was helpful and available any time we had questions. Truly a fabulous location, gorgeous water views, relaxing and just what we all were hoping for. Lastly, we brought our 36' power boat over from Annapolis and easily got in and out of of the deep water dock.

  • Submitted: Aug 5, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
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Washington, DC

Beautiful retreat on the shore

  • 5 of 5

Our organization spent the week at Martin Point Farm, which was the perfect setting for our meetings and activities. We absolutely enjoyed the peace and beauty of the point and being completely surrounded by water, as well as the historic house full of character. We were able to fit a large group in the house and spent lots of time on the expansive porches. Everything went very smoothly and the owner and caretaker were always accessible and very helpful, which was much appreciated considering all the logistics when organizing for such a large group.

  • Submitted: Oct 6, 2015
  • Stayed: Sep 2015
  • Source: VRBO, from HomeAway
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Baltimore, MD 21212

The Best of the Eastern Shore

  • 5 of 5

Our family has been enjoying the beauty, and seclusion of Martins Point for many years. The historic house with its classic porches, and living spaces, the pool surrounded by a unique blend of land and water, and the opportunity to interact in many activities on the extensive property and surrounding waters as well as the nearby attractive historic communities, keep us coming back.

  • Submitted: Sep 11, 2015
  • Stayed: Aug 2015
  • Source: VRBO, from HomeAway
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0 0

An Enchanting Place

  • 5 of 5

We picked Martins Point for our family reunion in July. The family consensus is that this was a perfect choice. (The family includes two teenagers, two grown children, and three toddlers.) The estate is on a beautiful point of land, oriented to enjoy 260-degree views of the water and every aspect of the Bay - birds, boats, swimming, fishing - this has it all. Anyone who loves the water will love this spot. The two cottages are beautifully appointed; the main house is as well. When it got hot, we enjoyed the large swimming pool. When the breeze blew, we were sailing the 19-foot sailboat from the private dock. The caretaker was super-friendly and made sure the tank in the skiff was filled with gas each day. He also helped us procure a half-bushel of fresh crabs! (He lives in a separate house on the estate far enough away so there's privacy.) We would love to go back every year.

  • Submitted: Aug 16, 2014
  • Stayed: Jul 2014
  • Source: VRBO, from HomeAway
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Rhinebeck, NY

Magical historic house on the eastern shore

  • 5 of 5

My family and friends have had the great good fortune to have stayed at this beautiful historic home twice now. It is the perfect place for a group to come together in a casual, laid back setting and enjoy the natural surrounding beauty. We took advantage of the beach, walking paths, water and day trips to neighboring small towns. But the best times we had were gathering for cocktails on the screened in porch overlooking the water or making big communal dinners that we then enjoyed in the dining room or bricked veranda. The house is not only filled with antiques but many personal photos and mementos belonging the the owner. We could the feel the deep roots around us - roots that go back 300 years or more. And it is those roots that made us feel deeply connected to our surroundings. Added to all of this was the attentive caretaker who saw to our every need. This is truly a unique home that we plan on coming back to again and again.

  • Submitted: Feb 14, 2014
  • Stayed: Aug 2013
  • Source: VRBO, from HomeAway
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Baltimore, MD 21212

Wonderful Easton Shore Family Retreat

  • 5 of 5

We have stayed at Martins Point with our children and grandchildren over many summers since discovering this unique waterfront homestead in the 1990s. Surrounded by water on three sides with a southwest exposure to the Choptank River, the property benefits from comfortable breezes during the summer, as well as well as outstanding views in all directions. The classic house with its upper and lower screen porches has all the amenities and comfort you need for a great family vacation. The pool and wonderful yard provide a center for family activities, and the location is ideal for boating, kayaking, sailing, fishing and other water activities. The cottages are great for grandchildren. There are opportunities to walk the entire property and beach with beautiful water views. This is one of the best locations for family members of all ages to experience the Easton Shore.

  • Submitted: Feb 10, 2014
  • Stayed: Jun 2013
  • Source: VRBO, from HomeAway
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Car: necessary

During fall and winter thousands of Canada geese and ducks winter in the coves and fields around the house. We've watched geese for many years but have never lost our love of watching them cup their wings as they come in to land.

The surrounding towns have a lot to offer. Easton, Oxford and St. Michael's are all within easy distance and sport restaurants, great antiquing and interesting shops. In St. Michael's, the Chesapeake Maritime Museum, only a few feet away from the Crab Claw, is always worth a visit. In the fall, the Blackwater Wildlife Refuge is a wonderful place to see a profusion of wildlife -- more geese and ducks than you can imagine. The trip there will also take you through one of the last undeveloped areas of the Eastern Shore.

Martins Point is located near Trappe, Maryland, less than two hour's drive from Washington, Baltimore and Philadelphia. Drive time from Baltimore Washington International airport is 90 minutes.

Other Activities: boating, shelling, biking, shopping, kayaking, wildlife viewing, hunting


Rates & Availability

Trappe Estate Rental Rates

Additional information about rental rates

Tax Rate 4.0%


  • $3,250-$6,500/week
  • May Day to Labor Day ............................................ $6,500/week
    Post-Labor Day to May Day .................................... $3,250/week
    Per day (post-Labor Day–May Day, 2 day min.).... $490-$550
    Thanksgiving, Christmas, New Years..................... $3,950/week

    Sailboat, kayaks, windsurfers and outboard skiff are separately available.

    Security deposit: $1,500.

    Note: Until confirmed, rates are subject to change without notice.
Available arrival
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Trappe Estate Accommodation and Amenities

Property Type:
  • estate
  • Guests provide their own meals
Location Type:
  • Rural
  • Waterfront
  • Away From It All
  • Air Conditioning
  • Clothes Dryer
  • Fireplace
  • Linens Provided
  • Parking
  • Parking Off Street
  • Washing Machine
  • Cooking Utensils
  • Dishwasher
  • Ice Maker
  • Microwave
  • Refrigerator
  • Dining Area
  • 6 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , combination tub/shower
    Bathroom 2 - toilet , combination tub/shower
    Bathroom 3 - toilet , combination tub/shower
    Bathroom 4 - toilet , combination tub/shower
    Bathroom 5 - toilet , combination tub/shower
    Bathroom 6 - toilet , combination tub/shower
    Bathroom 7 - toilet
  • 8 Bedrooms, Sleeps 15
  • Bedroom 1 - 1 queen
  • The house and cottages include 8 bedrooms and can accommodate 15 guests. Beds: * Queen Bed * Double Bed (2) * Twin/Single Bed (9) * Convertible Bed (2) * Crib
  • CD Player
  • DVD Player
  • Television
  • VCR
  • Video Library
  • Barbecue
  • Outdoor Grill
  • Porch / Veranda
  • children welcome
  • non smoking only
  • pets not allowed
  • wheelchair accessible
Pool / Spa:
  • Private Pool
  • arboretum
  • autumn foliage
  • bay/sound
  • churches
  • cinemas
  • forests
  • live theater
  • museums
  • restaurants
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • outlet shopping
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • groceries
  • hospital
Sports & Adventure Activities:
  • cycling
  • fishing
  • fly fishing
  • golf
  • hiking
  • hunting
  • jet skiing
  • pier fishing
  • sailing
  • sound/bay fishing
  • swimming
  • water skiing
  • wind-surfing
Our O'Day sailboat, kayaks, windsurfers and outboard skiff are also available for rental if you don't have a boat and would like to get out on the water. There is also: Window air conditioning units for every bedroom and public rooms, Wood Fireplace: Firewood is provided at no additional charge, Parking for RV/Boat/Trailer, Elevator: There is a stairway lift to the second floor, Fully equipped Kitchen, Two refrigerators and a freezer, Catering Available: Our caretaker is available to cater simple dinners such as BBQ, crabs, etc. Cost is separately negotiated with him, Charcoal BBQ Grill: Webber grill, Deck/Patio: Adjoins main house and pool, Lanai: First floor screen porch functions as a summer dining area. Second floor screened porch is an outdoor living room fully furnished with wicker and a porch swing, Martins Point is on a tributary of the Chesapeake Bay and is surrounded by water on three sides, facing a sheltered cove and our private beach.

Learn more about this vacation rental at the owner's website:

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