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Vacation Rentals in St. Michaels

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St Michaels Premier Waterfront home with pool and dock – Property 138986

  • St. Michaels rental - house, 5 bedrooms, sleeps 10, 4 bathrooms, river, pool
  • Calendar Last Updated On: May 22, 2012
This wonderful traditional Manor house is surrounded by water. Built on a point overlooking the Miles River and Long Haul Creek, means water views from every...

Elegant, Waterfront, Spacious, Cottage with Pool & Pier – Property 115575

  • St. Michaels rental - cottage, 3 bedrooms, sleeps 7, 2 bathrooms, town, waterfront, pool
  • Calendar Last Updated On: May 22, 2012
The Cottage at Long Haul is a charming 3 bedroom home situated on 6 acres within minutes of historic St. Michael's, MD on the Chesapeake Bay.

Estate residence on St. Michaels Harbor – Property 264058

  • St. Michaels rental - house, 6 bedrooms, sleeps 12, 6 bathrooms, 1 half bath, downtown, town, pool
  • $4,500 - $5,000/week
  • Calendar Last Updated On: May 22, 2012
This spacious 8000 sq. ft., 3 story home has beautiful harbor views of charming St. Michaels Harbor. A great home for family gatherings, corporate retreats or a...

'Sandy Pines' Lovely 4 BR Waterfront Home on Sandy Beach w/Pool, Dock – Property 314049

  • St. Michaels rental - house, 4 bedrooms, sleeps 9, 3 bathrooms, river, waterfront, pool
  • $2,600 - $4,600/week
  • Calendar Last Updated On: May 21, 2012
Sandy Pines, with its own waterfront, dock, and swimming pool, offers a peaceful retreat within the quiet natural beauty of the Chesapeake Bay region.

Charming historic farmhouse just minutes from all St. Michaels has to offer – Property 3001756

  • St. Michaels rental - farmhouse, 2 bedrooms, sleeps 4, 1 bathroom, town, waterfront, garden
  • $900 - $1,500/week
  • Calendar Last Updated On: May 21, 2012
Just blocks from the heart of historic St. Michaels, Split Rail is the perfect place to get away and stay! True to victorian homes, this c.

Premium Waterfront Estate Property - $7,250 Weekly – Property 388823

  • St. Michaels rental - estate, 5 bedrooms, sleeps 10, 4 bathrooms, 3 half baths, accept credit card, waterfront
  • $5,500 - $7,250/week
  • Calendar Last Updated On: May 19, 2012
The Cove At St. Michaels is a magnificent professionally decorated 15.5 acre estate property, just a 15 minute drive to the center of the Town of St.

St. Michael's premier in town summer vacation cottage! – Property 287681

  • St. Michaels rental - cottage, 2 bedrooms, sleeps 4, 2 bathrooms, downtown, pool
  • $1,400 - $1,500/week
  • Calendar Last Updated On: May 19, 2012
Harbor Hideaway's in town location is a rare find! HH's in town location is just steps away from everything that St. Michael's has to offer!

Historic Waterfront Home in St. Michaels – Property 123352

  • St. Michaels rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, river, waterfront, pool
  • $1,800 - $3,000/week
  • Calendar Last Updated On: May 18, 2012
Cranford on the Miles is a waterfront home located on 3+ acres in St. Michaels. Fully renovated, there is a Master Bedroom with king bed, sitting room, and private...

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

  • St. Michaels rental - estate, 1 bedroom, sleeps 12, 1 bathroom, waterfront, pool
  • $3,000 - $4,700/week
  • Calendar Last Updated On: May 18, 2012
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...

Waterfront Country Cottage Close To St Michaels – Property 185818

  • St. Michaels rental - cottage, 3 bedrooms, sleeps 6, 3 bathrooms, village, waterfront, terrace
  • $2,304 - $2,556/week
  • Calendar Last Updated On: May 21, 2012
The sage green color of this adorable cottage tells you right away that this is not your ordinary vacation home. The charming exterior gives way to a gracious, cozy...

Magnificent Vacation Rental Estate home - 'Elmslac' - dock, pool and privacy – Property 234152

  • St. Michaels rental - estate, 7 bedrooms, sleeps 14, 5 bathrooms, 2 half baths, river, waterfront, pool
  • $6,500/week
  • Calendar Last Updated On: May 11, 2012
This gorgeous grand estate home called 'Elmslac'is surrounded by huge old shady trees and lots of water! Imagine driving down a country lane and over a wooden...

'Chez Bonheur' magnificent 5 bedroom home on 1000 acre estate with pool and dock – Property 909425

  • St. Michaels rental - house, 6 bedrooms, sleeps 6, 2 bathrooms, 2 half baths, river, rural, waterfront, pool
  • $7,000/week
  • Calendar Last Updated On: May 11, 2012
'Chez Bonheur' Estate Only minutes from the famous historic “Chestertown”, this magnificent 1000 acre estate -' CHEZ BONHEUR' is both a wildlife sanctuary and...

Europa on the Beach - Architectural contempory home on the Chesapeake Bay – Property 234151

  • St. Michaels rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, garden
  • $3,500/week
  • Calendar Last Updated On: May 11, 2012
Tidewater Vacations Inc is proud to manage this wonderful vacation home. A striking balance between modernism and industrial styled architecture, Europa is a...

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

  • St. Michaels rental - estate, 5 bedrooms, sleeps 10, 3 bathrooms, waterfront, air-conditioning
  • Calendar Last Updated On: May 8, 2012
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...

Chesapeak Bay oriented waterfront home with private pool and deep water dock – Property 376538

  • St. Michaels rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, accept credit card, balcony
  • $3,800/week
  • Calendar Last Updated On: May 2, 2012
Large, lovely home situated on over 2 acres on Dunn's Cove off Harris Creek leading to the Chesapeake Bay. Two master suites with private baths, 3rd waterside...

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

  • St. Michaels rental - estate, 4 bedrooms, sleeps 8, 4 bathrooms, rural, waterfront, pool
  • Calendar Last Updated On: May 2, 2012
Luxurious estate five minutes from St. Michaels features a traditional Eastern Shore telescope house with formal living and dining rooms, family room and large...

St. Michaels Premier Waterfront estate close to town, golfcourse, Harbor,Museum – Property 113980

  • St. Michaels rental - estate, 6 bedrooms, sleeps 12, 5 bathrooms, 1 half bath, accept credit card, resort, waterfront
  • Calendar Last Updated On: May 2, 2012
Bay Cottage, St. Michaels premier waterfront vacation estate is now offered to groups and families for private enjoyment as a vacation home.

Large Waterfront Estate Located on Miles River – Property 285484

  • St. Michaels rental - house, 6 bedrooms, sleeps 12, 4 bathrooms, accept credit card, waterfront
  • $3,000 - $5,745/week
  • Calendar Last Updated On: May 1, 2012
Located just minutes from St. Michaels, Maryland you and your family can have an authentic Eastern Shore experience at our waterfront farm estate while still just a...

Large Luxury Waterfront Cape Cod with New Pool and Beautiful Sunsets – Property 233398

  • St. Michaels rental - house, 5 bedrooms, sleeps 10, 4 bathrooms, town, waterfront, pool
  • $3,500 - $6,300/week
  • Calendar Last Updated On: Apr 26, 2012
'Inn Harmony' is located on 4 pristine waterfront acres 2 miles from the center of St. Michaels, Maryland. Situated on a tributary of the Chesapeake Bay (the...

Endless Waterfront Sunsets on Eastern Bay!! – Property 246578

  • St. Michaels rental - house, 2 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, accept credit card, village, waterfront
  • $1,750 - $2,800/week
  • Calendar Last Updated On: Apr 23, 2012
Come enjoy the quaintness of Claiborne, MD, just 5 minutes from historic St. Michaels, on the beautiful Eastern Shore of MD. Slow your pace and enjoy a leisurely...
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