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Vacation Rentals in St. Michaels

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

  • St. Michaels rental - cottage, 3 bedrooms, sleeps 8, 1 half bath, town, waterfront, swimming pool
  • Calendar Last Updated On: Jul 17, 2008
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.

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

  • St. Michaels rental - house, 4 bedrooms, sleeps 10, 3 bathrooms, river, waterfront, swimming pool
  • Calendar Last Updated On: Jul 10, 2008
Sandy Pines, with its own sandy beach, dock, and swimming pool, offers a peaceful retreat within the quiet natural beauty of the Chesapeake Bay region.
SPECIAL OFFER! Special 'In Season' Rate July 12 - August 30

Waterfront Horse Farm Estate - A Slice Of Heaven On Earth – Property 139007

  • St. Michaels rental - estate, 5 bedrooms, sleeps 12, 3 bathrooms, 1 half bath, waterfront, accept credit card
  • $5,200/week
  • Calendar Last Updated On: Jun 23, 2008
Halo's Haven is a true piece of Heaven!! Bring your boat and your bathing suit. Twenty picturesque acres on a beautiful point of land off of the Chesapeake Bay near...

Waterfront Country Cottage Close To St Michaels – Property 185818

  • St. Michaels rental - cottage, 3 bedrooms, sleeps 6, 3 bathrooms, village, waterfront, air-conditioning
  • $1,392 - $1,995/week
  • Calendar Last Updated On: Jun 20, 2008
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...

House rental in Wittman Village Wittman - Charming Designer Decorated Retreat – Property 166854

  • St. Michaels rental - house, 3 bedrooms, sleeps 6, 1 bathroom, 1 half bath, rural, village, swimming pool
  • $900/week
  • Calendar Last Updated On: May 31, 2008
Newly remodeled and beautifully furnished, this quaint retreat is located in a quiet, rural village full of friendly and fun-loving folks, where watermen come and go...

Charming Cozy Cove Cottage Romantic Escape – Property 169274

  • St. Michaels rental - cottage, 3 bedrooms, sleeps 6, 1 bathroom, village, waterfront, swimming pool
  • $1,275 - $1,500/week
  • Calendar Last Updated On: May 30, 2008
This charming and quaint 2 story cottage is located minutes from historic St. Michael's. The interior of the Cottage was newly renovated without compromising the old...

Great Vacation Value under $2000/wk in St. Michaels – Property 189650

  • St. Michaels rental - cottage, 3 bedrooms, sleeps 7, 2 bathrooms, river, waterfront, accept credit card
  • $1,409 - $1,994/week
  • Calendar Last Updated On: May 9, 2008
At the end of a meandering lane lies this adorable home waiting for you and your family to discover our Eastern Shore lifestyle!

5BR Waterfront Estate with Pool, Dock, minutes to St. Michael's – Property 110578

  • St. Michaels rental - estate, 5 bedrooms, sleeps 12, 4 bathrooms, 1 half bath, town, waterfront, accept credit card
  • $2,362 - $6,110/week
  • Calendar Last Updated On: Apr 14, 2008
This property has it all! Located just minutes to St. Michaels, yet privately situated at the end of Yacht Club Road, you will enjoy the best of both worlds.

In town St. Michaels, Waterfront Home, Dock and Great Views – Property 123353

  • St. Michaels rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, village, waterfront, accept credit card
  • $1,882 - $2,882/week
  • Calendar Last Updated On: Mar 31, 2008
Uniquely located within walking distance of St. Michael's and on the Miles River, Swan Harbor provides its guests the best of both worlds.

Waterfront Home with Private Dock – Property 123352

  • St. Michaels rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, river, waterfront, swimming pool
  • $2,000 - $2,700/week
  • Calendar Last Updated On: Jan 23, 2008
Get away and relax at Cranford on the Miles, a piece of true Eastern shore elegance dating back to 1840. Tucked away on over 3 park-like acres, you’ll be enchanted...

Swan Cove Waterfront Estate - Family Reunions & Weddings! – Property 170393

  • St. Michaels rental - estate, 22 bedrooms, sleeps 40, 17 bathrooms, 1 half bath, town, waterfront, accept credit card
  • $8,000/week
  • Calendar Last Updated On: Dec 17, 2007
At the end of a long tree-lined drive, against the beautiful Little Choptank River, lies Swan Cove. The historic charm of this 25-acre farm has been enhanced by a...

Finest Waterfront Estate in St. Michaels, MD – Property 165386

  • St. Michaels rental - estate, 6 bedrooms, sleeps 12, 4 bathrooms, rural, waterfront, accept credit card
  • $6,725/week
  • Calendar Last Updated On: Dec 17, 2007
Horseshoe Bay, St. Michaels, MD ------ Horseshoe Bay is very private and it includes a 100-acre private island and offers one of the best waterfront vacation...

Exclusive St. Michael's Getaway Vacation – Property 169533

  • St. Michaels rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, waterfront, accept credit card
  • $3,625/week
  • Calendar Last Updated On: Dec 17, 2007
Enjoy yourself while staying at this beautiful waterfront property. Lounge around the pool or go crabbing off of the private dock.

St. Michaels Premier- Waterfront! – Property 113980

  • St. Michaels rental - estate, 5 bedrooms, sleeps 11, 5 bathrooms, 1 half bath, accept credit card, swimming pool
  • Calendar Last Updated On: Dec 17, 2007
Bay Cottage, St. Michaels premier waterfront vacation estate is now offered to groups and families for private enjoyment as a vacation home.

The Nourse Farm at St. Michaels – Property 124533

  • St. Michaels rental - house, 7 bedrooms, sleeps 20, 6 bathrooms, waterfront, swimming pool
  • Calendar Last Updated On: Dec 17, 2007
Located just minutes away from historical St. Michaels, Maryland. Set on 70 acres, this beautiful Tudor style home has one-half mile of waterfront property.

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

  • St. Michaels rental - estate, 5 bedrooms, sleeps 10, 3 bathrooms, waterfront, swimming pool
  • Calendar Last Updated On: Dec 17, 2007
Longview is a magnificent three acre waterfront estate in St. Michaels, Maryland. This Dutch Colonial home boasts 5 bedrooms, 3 acres of lawn and 800 feet of...

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

  • St. Michaels rental - house, 5 bedrooms, sleeps 10, 4 bathrooms, river, swimming pool
  • Calendar Last Updated On: Dec 16, 2007
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...

Charming, private waterfront home, close to St. Michaels, Oxford, and Easton. – Property 165697

  • St. Michaels rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, river, rural, air-conditioning
  • $2,000 - $3,000/week
  • Calendar Last Updated On: Dec 16, 2007
Charming, private waterfront home on creek leading to the Tred Avon River. Deepwater dock with boat lift, water and electricity.

Eastern Shore Estate Home with Dock, Boathouse, Pool – Property 131746

  • St. Michaels rental - estate, 3 bedrooms, sleeps 8, 4 bathrooms, 1 half bath, river, waterfront, accept credit card
  • $4,552 - $5,752/week
  • Calendar Last Updated On: Dec 13, 2007
The blue gates greeting you at the driveway provide a hint of what you'll find at the end of the meandering lane--a classic home with a twist of French Country...

Country Cottage outside St. Michaels, sleeps 8, under $2000/week – Property 68404

  • St. Michaels rental - cottage, 4 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, Includes row boat and bikes, home is pet friendly, sleeps 8
  • $1,190 - $2,015/week
  • Calendar Last Updated On: Jan 4, 2008
Caulks Cove is a delightful getaway cottage with broad sweeping views of Caulk's Cove which leads to Broad Creek. An inviting deck with shade trees abound coaxing...
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