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...

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.

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...

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...

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

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...

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 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...

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...

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...

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...

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...

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...

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...

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...

This charming cottage located just outside Historic Cambridge, Maryland is just the ticket for a relaxing getaway for friends or a small family.

Sprawling over several acres with sweeping views of Eastern Bay, Cabin Cove Manor is the perfect setting for your next family celebration or getaway with friends.

Windswept--a beautiful home with new hardwood floors, cheery kitchen with banquette and over 3,000 square feet of living space welcomes you to one of the best...