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Vacation Rentals in Maryland

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Historic Oxford Waterfront Estate welcoming 1-2 couples OR up to 12 guests – Property 3622929

  • Maryland rental - estate, 6 bedrooms, sleeps 12, 5 bathrooms, 1 half bath, Private Pool, Lawn / Garden
  • $2,450 - $4,900/week
  • Calendar Last Updated On: Apr 16, 2014
Bonfield Manor is located at the entrance of Oxford, a half mile walk or bike ride to restaurants,shops and the Riverview Ave beach.

Exceptional Waterfront Estate – Property 272472

  • Maryland rental - estate, 5 bedrooms, sleeps 10, 6 bathrooms, 2 half baths, pets considered, Hot Tub
  • $5,500/week
  • Calendar Last Updated On: Apr 15, 2014
This home features a gourmet kitchen with 'top of the line' appliances (two Sub Zeroes, two dishwashers, wine cooler, etc.) The beautiful living spaces include an...

Willows on the Miles - Private, waterfront farmhouse estate- Miles River – Property 966959

  • Maryland rental - estate, 6 bedrooms, sleeps 12, 3 bathrooms, pets considered, Waterfront
  • Calendar Last Updated On: Apr 17, 2014
This private, waterfront estate is located on the Miles River and just minutes from St. Michaels. Features an in-ground swimming poool, screened porch, sweeping...

Eastern Shore Waterfront Estate, Private Beach, Deep Water – Property 211778

  • Maryland rental - estate, 8 bedrooms, sleeps 15, 6 bathrooms, 1 half bath, wheelchair accessible, Rural, Waterfront
  • Calendar Last Updated On: Apr 13, 2014
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...

*****10% off stays of 3 nights or more for April and May****** – Property 3021814

  • Maryland rental - estate, 3 bedrooms, sleeps 9, 2 bathrooms, 1 half bath, pets considered, Hot Tub
  • $2,400 - $3,750/week
  • Calendar Last Updated On: Apr 17, 2014
On the upper reaches of the Eastern Shore's beautiful Broad Creek lies the pet-friendly mini-estate known as Broad Creek Lodge.
SPECIAL OFFER! Up to 10% off multiple Villa bookings! April 4 - May 4

Tranquil Ocean View Villas With Flexible Floor Plans, Choose From 1 To 8 Bedroom – Property 3662371

  • Maryland rental - estate, 8 bedrooms, sleeps 28, 5 bathrooms, wheelchair accessible, Lawn / Garden
  • $1,395 - $1,995/week
  • Calendar Last Updated On: Apr 10, 2014
Located in historic downtown Ocean City, Chateau Surf is one of OC’s genuine beach homes. This classic 1929 estate recently underwent a full renovation.

Luxurious and Extremely Private Waterfront Estate – Property 942769

  • Maryland rental - estate, 8 bedrooms, sleeps 20, 7 bathrooms, 2 half baths, pets considered, Rural, Waterfront
  • $7,450 - $11,500/week
  • Calendar Last Updated On: Apr 9, 2014
Deep Neck Point is a very private luxury waterfront retreat able to comfortably accommodate up to 20 guests. Located on a private 60 acre peninsula that reaches out...

Bay Cottage, St. Michaels, Md Waterfront Vacation Retreat: Pool, Dock,Farm, Bike – Property 3724624

  • Maryland rental - estate, 6 bedrooms, sleeps 12, 5 bathrooms, 1 half bath, Resort, Rural, Village, Private Pool
  • $4,050 - $6,350/week
  • Calendar Last Updated On: Apr 8, 2014
Bay Cottage Waterfront Vacation Retreat & Farm is surrounded with water on East, North, and West with dock, pier, waterside pool, culinary herb and vegetable...

Magnificent Vacation Rental home - 'Compass Rose' with pool and dock – Property 234152

  • Maryland rental - estate, 5 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, wheelchair accessible, Downtown, River, Town, Waterfront
  • $5,502/week
  • Calendar Last Updated On: Apr 6, 2014
The Compass Rose - another exclusive vacation rental home by Tidewater Vacations in St Michaels, md. Wow, wow, wow! Brand new to the vacation market and just a...

Charming, Waterfront Carriage House. Pet Friendly – Property 3589066

  • Maryland rental - estate, 2 bedrooms, sleeps 7, 2 bathrooms, pets considered, Hot Tub
  • $1,600 - $2,200/week
  • Calendar Last Updated On: Mar 31, 2014
Come stay in our beautiful, clean new carriage house situated on a 2 acre waterfront estate which is gated and fenced in. Bring the kids!

Genteel, 30 Acre Waterfront Estate, Private, Close to Easton, Shops, and Dining – Property 3589723

  • Maryland rental - estate, 6 bedrooms, sleeps 12, 6 bathrooms, Private Pool, Lawn / Garden
  • $5,000 - $6,000/week
  • Calendar Last Updated On: Mar 26, 2014
'Boston Farm' is situated on the tip of a peninsula on Trappe Creek, which opens to the Choptank River and on to the Chesapeake Bay.

Luxury home with pool and deep water dock. – Property 336403

  • Maryland rental - estate, 4 bedrooms, sleeps 8, 4 bathrooms, Rural, Private Pool
  • $5,500/week
  • Calendar Last Updated On: Jan 29, 2014
Luxurious estate five minutes from St. Michaels features a traditional Eastern Shore telescope house with formal living and dining rooms, family room and large...

Beautiful Luxury Estate Home Minutes to Washington DC. DARNESTOWN. N. POTOMAC – Property 3611024

  • Maryland rental - estate, 4 bedrooms, sleeps 8, 4 bathrooms, 1 half bath, Lawn / Garden, Air Conditioning
  • $5,355/week
  • Calendar Last Updated On: Oct 14, 2013
Welcome to and engulf yourself in the classic elegance of this fully furnished 4 bedroom, 4.5 bath luxury home located in beautiful Darnestown, Maryland north...

Longview -- Waterfront Estate w/ Pool & 3+ Acres – Property 109333

  • Maryland rental - estate, 5 bedrooms, sleeps 10, 3 bathrooms, Waterfront, Air Conditioning
  • Calendar Last Updated On: May 28, 2013
Longview is a magnificent three acre waterfront estate in St. Michaels, Maryland. This Dutch Colonial home boasts 4 bedrooms, 3 acres of lawn and 800 feet of...

Waterfront vacation on a private, historic estate – Property 297871

  • Maryland rental - estate, 5 bedrooms, sleeps 12, 3 bathrooms, 1 half bath, accept credit card, pets considered
  • Calendar Last Updated On: May 28, 2013
In ground swimming pool with pool house, private beach areas, sweeping lawns and a long private lane are some of the features of this home. Regal Historic Estate:...
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