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...

At the end of a meandering lane lies this adorable home waiting for you and your family to discover our Eastern Shore lifestyle!

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...

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...

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...

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 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...

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

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.

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.

Caulks Cove is a delightful getaway cottage with broad sweeping views of Caulk's Cove which leads to Broad Creek. An inviting deck with shade trees abound coaxing...

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...

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,...

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...