Located on the outskirts of the town proper of St. Michaels, this fantastic family vacation compound provides everything you need for a true Eastern Shore getaway.

A deep water pier with picturesque views make this a truly special spot for a weekend getaway, or mini vacation. Couples love the cozy feeling this cottage gives,...

Only 1 hour from Washington, DC, come enjoy this beautiful, luxury Chesapeake Bay waterfront home with 180 degree views of the water.

This expansive five bedroom home provides all the modern conveniences of home only with Eastern Chesapeake Bay as the setting.

A traditional Eastern Shore farmhouse, Bushey Heath Farm is a rustic retreat just miles from St. Michaels. Tucked away on a very private 90 acres, this is the type...

A restful spot overlooking the Tred Avon River, between Easton and St. Michaels. A great central location find if you are coming into the area for one of the local...

A great little cottage with big amenities, Clearview is the answer to your getaway needs. Swimming pool, hot tub, fresh decorating and painting, and views that go...

The ever-changing Chester River is the focal point of the house. Watermen called this section of the river “Moon Bay," hence the name The River House on Moon Bay.

This charming property located just outside of St. Michaels has all you need for plug-n-play fun for your family! A playgym, private swimming pool, dock, and two...

Harbor Hideaway(HH) is a charming story and a half cottage that has been completely renovated with amenities that will help ensure a great time on your St.

Hampden is the oldest brick structure in Talbot County. Step back in time, circa 1663, and wrap yourself around the charm and ambience of this gentleman's estate.

With over 2500 feet of private shoreline, on 25 acres, city dwellers will definitely have room to roam and not feel encumbered by this wonderful rural farm.

This charming cottage is the ideal place for a couple or small group looking for respite and relaxation. On the outskirts of Tilghman Island, come to Choptank...

This little gem on the banks of Soltitude Creek is a perfect family getaway! With a pool, hot tub, and canoe for exploring the creeks and tributaries of the Tred...

This waterfront cottage has great cove views of Soltitude Creek, aptly named for the peace and serenity it delivers. Great waterviews with glass doors virtually...

This charming home in the heart of Tilghman Island is the perfect answer to your need to escape! Charming throughout, this 4 bedroom home has been lovingly but...

A sprawling one level home within blocks of the historic district of St. Michaels, Swan Harbor is a rare to find waterfront vacation home with walking proximity to...

This light filled contemporary home has a wonderful shaded yard and beautiful deck high up in the trees. A great destination unto itself Swift Haven provides a host...