Vacation Rentals in St. Michaels

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...

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...

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.

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...

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.

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...

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...

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...