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Vacation Rentals in St. Michaels

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Fantastic Family Compound 1/2 mile to St. Michaels, Pool, Dock, Hot tub – Property 7004796

  • St. Michaels rental - house, 5 bedrooms, sleeps 10, 4 bathrooms, dock boatslip, DVD
  • $2,839 - $6,271/week
  • Calendar Last Updated On: Nov 21, 2009
Located on the outskirts of the town proper of St. Michaels, this fantastic family vacation compound provides everything you need for a true Eastern Shore getaway.

Beautifully appointed vacation home outside St. Michaels – Property 7022556

  • St. Michaels rental - house, 6 bedrooms, sleeps 12, 5 bathrooms, dock boatslip, DVD
  • $3,251 - $5,307/week
  • Calendar Last Updated On: Nov 21, 2009

Budget friendly cottage getaway, with rowboat included! – Property 7022552

  • St. Michaels rental - cottage, 4 bedrooms, sleeps 8, 2 bathrooms, dock boatslip, DVD
  • $1,315 - $1,940/week
  • Calendar Last Updated On: Nov 21, 2009
A deep water pier with picturesque views make this a truly special spot for a weekend getaway, or mini vacation. Couples love the cozy feeling this cottage gives,...

Fun house outside St. Michaels, pool, dock, hot tub, ping pong – Property 7007440

  • St. Michaels rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, dock boatslip, DVD
  • $1,473 - $3,345/week
  • Calendar Last Updated On: Nov 21, 2009
This little gem on the banks of Soltitude Creek is a perfect family getaway! With a pool, hot tub, and canoe for exploring the creeks and tributaries of the Tred...

Conveniently located home between Easton and St. Michaels, private with Tred Avon views! – Property 7015502

  • St. Michaels rental - cottage, 3 bedrooms, sleeps 6, 2 bathrooms, dock boatslip, DVD
  • $1,375 - $2,275/week
  • Calendar Last Updated On: Nov 21, 2009
A restful spot overlooking the Tred Avon River, between Easton and St. Michaels. A great central location find if you are coming into the area for one of the local...

Sweeping Chesapeake Bay views with Sandy Beach,dock, pool. – Property 7004795

  • St. Michaels rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, dock boatslip, DVD
  • $1,913 - $3,998/week
  • Calendar Last Updated On: Nov 21, 2009
This expansive five bedroom home provides all the modern conveniences of home only with Eastern Chesapeake Bay as the setting.

90 acre farm with wrap around views, 5 minutes to St. Michaels, pool, dock – Property 7004794

  • St. Michaels rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, dock boatslip, DVD
  • $1,453 - $3,325/week
  • Calendar Last Updated On: Nov 21, 2009
A traditional Eastern Shore farmhouse, Bushey Heath Farm is a rustic retreat just miles from St. Michaels. Tucked away on a very private 90 acres, this is the type...

Single family getaway! Pool, playgym, dock, and more! – Property 7004805

  • St. Michaels rental - cottage, 3 bedrooms, sleeps 6, 1 bathroom, dock boatslip, DVD
  • $1,328 - $2,333/week
  • Calendar Last Updated On: Nov 21, 2009
This charming property located just outside of St. Michaels has all you need for plug-n-play fun for your family! A playgym, private swimming pool, dock, and two...

Bungalow in heart of historic district – Property 7004802

  • St. Michaels rental - cottage, 2 bedrooms, sleeps 4, 2 bathrooms, DVD, grill
  • $1,150 - $1,175/week
  • Calendar Last Updated On: Nov 21, 2009
Harbor Hideaway(HH) is a charming story and a half cottage that has been completely renovated with amenities that will help ensure a great time on your St.

Historic Estate with 5BR's, pool, hot tub, gourmet kitchen and deep water dock. – Property 7004801

  • St. Michaels rental - house, 5 bedrooms, sleeps 14, 4 bathrooms, dock boatslip, DVD
  • $2,603 - $5,878/week
  • Calendar Last Updated On: Nov 21, 2009
Hampden is the oldest brick structure in Talbot County. Step back in time, circa 1663, and wrap yourself around the charm and ambience of this gentleman's estate.

Expansive 4 bedroom home 5 blocks to town of St. Michaels, wide water views. – Property 7004814

  • St. Michaels rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, dock boatslip, DVD
  • $1,265 - $2,190/week
  • Calendar Last Updated On: Nov 21, 2009
A sprawling one level home within blocks of the historic district of St. Michaels, Swan Harbor is a rare to find waterfront vacation home with walking proximity to...

Light Filled Contemporary with 4 Queen bedrooms, dock,pool – Property 7004815

  • St. Michaels rental - house, 4 bedrooms, sleeps 9, 2 bathrooms, dock boatslip, DVD
  • $1,747 - $3,776/week
  • Calendar Last Updated On: Nov 21, 2009
This light filled contemporary home has a wonderful shaded yard and beautiful deck high up in the trees. A great destination unto itself Swift Haven provides a host...

Very private 25 acre home with sunset views, deep water dock, pool – Property 7004811

  • St. Michaels rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, dock boatslip, DVD
  • $1,653 - $3,350/week
  • Calendar Last Updated On: Nov 21, 2009
With over 2500 feet of private shoreline, on 25 acres, city dwellers will definitely have room to roam and not feel encumbered by this wonderful rural farm.

Contemporary Cottage with pool, tranquil views and great nature watching! – Property 7014511

  • St. Michaels rental - cottage, 3 bedrooms, sleeps 8, 2 bathrooms, dock boatslip, DVD
  • $1,646 - $3,336/week
  • Calendar Last Updated On: Nov 21, 2009
This waterfront cottage has great cove views of Soltitude Creek, aptly named for the peace and serenity it delivers. Great waterviews with glass doors virtually...

Cottage with pool, hot tub and great water – Property 7018652

  • St. Michaels rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, dock boatslip, DVD
  • $1,704 - $3,576/week
  • Calendar Last Updated On: Nov 21, 2009
This charming cottage has a great location, just minutes to St. Michaels or Easton, and offers much in the way of family entertainment--pool, hot tub, private dock...

Waterfront Cottage minutes to St. Michaels, hot tub – Property 7018650

  • St. Michaels rental - cottage, 3 bedrooms, sleeps 5, 2 bathrooms, DVD, fireplace
  • $1,358 - $2,158/week
  • Calendar Last Updated On: Nov 21, 2009

One level vacation home outside St. Michaels, pool, wide views, great breezes – Property 7007442

  • St. Michaels rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, DVD, fireplace
  • $1,744 - $3,773/week
  • Calendar Last Updated On: Nov 21, 2009
A simple one level home offering great expansive water views, close in location to St. Michaels, waterfront pool and secluded privacy.

Hideaway on Long Haul Creek, minutes to town – Property 7004799

  • St. Michaels rental - cottage, 3 bedrooms, sleeps 6, 3 bathrooms, dock boatslip, DVD
  • $1,295 - $1,920/week
  • Calendar Last Updated On: Nov 21, 2009
There is nothing to be crabby about when staying at this restful spot just outside St. Michaels. Comfortably furnished yet priced for the budget conscious...

Waterfront cottage with pool and hot tub, close to town of St. Michaels – Property 7004810

  • St. Michaels rental - cottage, 3 bedrooms, sleeps 6, 3 bathrooms, dock boatslip, DVD
  • $1,401 - $2,976/week
  • Calendar Last Updated On: Nov 21, 2009
This cottage is close to the town of St. Michaels and offers big amenities you would normally find in an estate rental home--a pool, hot tub, gourmet kitchen, and...

Restored farmhouse with pool, poolhouse, dock, kayak and more! – Property 7004804

  • St. Michaels rental - house, 5 bedrooms, sleeps 10, 4 bathrooms, dock boatslip, DVD
  • $2,895 - $5,407/week
  • Calendar Last Updated On: Nov 21, 2009
History and modern convenience blend perfectly in this home, giving you a healing dose of charm and tranquility, with the luxury of newly renovated baths, kitchens...
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