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Vacation Rentals in St. Michaels

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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
  • Calendar Last Updated On: Nov 18, 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...

Great Fall Getaway home minutes to St. MIchaels – Property 189650

  • St. Michaels rental - cottage, 3 bedrooms, sleeps 7, 2 bathrooms, river, waterfront, accept credit card
  • $921 - $2,159/week
  • Calendar Last Updated On: Oct 14, 2008
At the end of a meandering lane lies this adorable home waiting for you and your family to discover our Eastern Shore lifestyle!

Available for the Obama Inauguration! Escape to the quiet Eastern Shore! – Property 110578

  • St. Michaels rental - estate, 5 bedrooms, sleeps 10, 4 bathrooms, 1 half bath, town, waterfront, accept credit card
  • $2,362 - $6,126/week
  • Calendar Last Updated On: Oct 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.

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 - $5,552/week
  • Calendar Last Updated On: Oct 14, 2008
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...
SPECIAL OFFER! Waterfowl Hunting Special St. Michaels! December 1 - February 1

Waterfowl Hunting Packages - St. Michaels, MD! – Property 207574

  • St. Michaels rental - estate, 5 bedrooms, sleeps 12, 5 bathrooms, waterfront, accept credit card
  • $4,725 - $6,725/week
  • Calendar Last Updated On: Sep 19, 2008
This beautiful point of land offers privacy, beautiful sunsets with all the activities that the Eastern Shore has to offer! There is boating, sailing, kayaking,...

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...

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.

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...

Luxury Pet Friendly Mini Estate, pool, dock, 3BR en suite – Property 68399

  • St. Michaels rental - private home, 3 bedrooms, sleeps 6, 4 bathrooms, Gourmet Kitchen, deep water dock, pool, dog runs, very private, steps to water
  • $1,676 - $4,476/week
  • Calendar Last Updated On: Oct 14, 2008
Your heart's desire comes this magnificent estate property, circa 1780. The owners have thought of everything you need for a perfect Eastern Shore...

Bloomfield--Conveniently located private mini estate, pool, dock tennis court – Property 68397

  • St. Michaels rental - private home, 3 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, Deep Water Dock, Tennis Court, Very Private, Pool, Fireplace
  • $1,854 - $4,514/week
  • Calendar Last Updated On: Oct 14, 2008
Bloomfield is a charming Eastern Shore Escape centrally located to the best of Talbot County but privately situated on a 4+ acre estate with tennis courts, private...

Lee Haven--Restored Farmhouse outside of Easton and St. Michaels, 5 bedrooms, pool, dock – Property 68417

  • St. Michaels rental - private home, 5 bedrooms, sleeps 12, 4 bathrooms, 1 half bath, 5BR, including spacious first floor master suite, lots of living spaces
  • $2,602 - $6,697/week
  • Calendar Last Updated On: Oct 14, 2008
This family compound has it all, 5 bedrooms, 4 1/2 baths, pool, dock, close to St Michaels and Easton and situated off of the Tred Avon.<br /> <br /> Beautifully...

Charming Bungalow in Heart of Historic District--Walk to town and shopping – Property 68414

  • St. Michaels rental - bungalow, 2 bedrooms, sleeps 4, 2 bathrooms, Walk to restaurants, shopping and the harbor. Great for biking, pet friendly
  • $810 - $1,193/week
  • Calendar Last Updated On: Oct 14, 2008
Just a stone's throw from the harbor and to the shopping district in St. Michaels, Harbor Hideaway is a charming 1940's bungalow that has been fully restored.<br...

My Blue Heron – Property 68422

  • St. Michaels rental - private home, 4 bedrooms, sleeps 8, 2 bathrooms, 1 half bath,
  • Calendar Last Updated On: Oct 14, 2008
Ensconced at water's edge on four acres of wooded privacy, this well laid out brick home reflects the attachment of, and attentive use by, its owners.<br /> <br...

Sunrise Cove – Property 68435

  • St. Michaels rental - private home, 3 bedrooms, sleeps 8, 3 bathrooms,
  • $1,608 - $2,585/week
  • Calendar Last Updated On: Oct 14, 2008
This spacious 2,500 square foot homes sits on 2 acres overlooking Solitude Creek. With a private dock and pool/hot tub you have everything you need for a relaxing...

Exclusive Private Estate Vacation Rental, pool, dock – Property 68413

  • St. Michaels rental - private home, 5 bedrooms, sleeps 10, 4 bathrooms, 1 half bath, Estate home in Talbot County, MD
  • $2,553 - $3,474/week
  • Calendar Last Updated On: Oct 14, 2008
The oldest existing brick house in Talbot County, Hampden awaits the history buff to discover all its secrets!<br /> <br /> Located on LaTrappe Creek, this 17th...

Bushey Heath Farm – Property 68400

  • St. Michaels rental - private home, 4 bedrooms, sleeps 8, 2 bathrooms,
  • $1,587 - $2,173/week
  • Calendar Last Updated On: Oct 14, 2008
The best of both worlds come with this Classic Cape Cod waterfront home. Conveniently located just minutes to St. Michaels for all the activities you desire, yet a...

1920's Farmhouse with pool, dock, playgym – Property 68419

  • St. Michaels rental - farmhouse, 3 bedrooms, sleeps 6, 1 bathroom, 1 half bath, Pool, Dock, Playgym
  • Calendar Last Updated On: Oct 14, 2008
Awaken to the rooster's subtle cries in the distance and share your morning coffee with the resident swans at "Mack's Landing" on Pot Pie Road.<br /> <br /> This...

Spectacular Large Family Home, Pool, Dock Wide Views – Property 68444

  • St. Michaels rental - private home, 5 bedrooms, sleeps 9, 3 bathrooms, 1 half bath, Expansive Water views, very private, sprawling one level home with pool and dock
  • $2,479 - $4,865/week
  • Calendar Last Updated On: Apr 16, 2008
Newly furnished, Whale Tail Farm is perfect for creating a memorable environment for your family vacation. With over 800' of shoreline on 7 1/2 acres, this 4,000...

Swan Harbor – Property 68436

  • St. Michaels rental - private home, 4 bedrooms, sleeps 8, 3 bathrooms, 4 BR Waterfront home, private dock, nearby community pool
  • $1,893 - $2,893/week
  • Calendar Last Updated On: Oct 14, 2008
Uniquely located within walking distance of St. Michaels and on the Miles River, Swan Harbor provides its guests the best of both worlds.
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