Vacation Rentals in St. Michaels

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, with its own sandy beach, dock, and swimming pool, offers a peaceful retreat within the quiet natural beauty of the Chesapeake Bay region.

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...

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...

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.

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...

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...

Enjoy yourself while staying at this beautiful waterfront property. Lounge around the pool or go crabbing off of the private dock.

Bay Cottage, St. Michaels premier waterfront vacation estate is now offered to groups and families for private enjoyment as a vacation home.

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 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...

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...

Miles Aweigh is a special property that offers all the comfort and privacy of an estate home--the pool, the private deep water dock, three queen en suite bedrooms,...

Barth's cottage is perfectly situated between St Michaels and Easton, waterfront just minutes from The Miles River off of Newcomb Creek.

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...

Welcome to Hudson Creek Cottage, a delightful and cozy cottage in the desirable Neck District of Dorchester County. This perfect year round waterfront retreat will...

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...

This family compound has it all, 6 bedrooms, 4 1/2 baths, pool, dock, close to St Michaels and Easton and situated off of the Tred Avon.<br /> <br /> Beautifully...

Ever wish you could step back in time? Just for a little while? At East Bonfield, you will feel transformed to an easier time, when kids played freely and were...