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.

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...

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...

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,...

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...

Your heart's desire comes this magnificent estate property, circa 1780. The owners have thought of everything you need for a perfect Eastern Shore...

The days are a little slower at Water's Edge. . .The home sits with water on three sides, you wake up to the quiet sound of the water lapping the shore.

Uniquely located within walking distance of St. Michaels and on the Miles River, Swan Harbor provides its guests the best of both worlds.

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...

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

A perfect family retreat, Cod's Point has so much to offer you'll want to stay all summer!<br /> <br /> Start your day by sipping your coffee and admiring the...

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...

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...

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...

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...

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...

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...