Upcoming Events
  October (save 10%!)
9-12 Columbus Day Weekend
10 Bark In the Park,EA
10 Wine and Food Festival
at Simpatico, SM
17 IronMan Competition (RESCHEDULED)
17 Tilghman Island Day, TI
18 Critter Release, TI
31 OysterFest, SM
13-15 Waterfowl Festival, EA
25-29 Thanksgiving on the Shore



A Bay Vacation...It's Better than the Beach!

Discover the quiet side of Maryland’s Eastern Shore and escape the hustle and bustle of a beach vacation! Sunrises and sunsets, miles of pristine shoreline, sophisticated small town charm and family friendly fun.  With an Eastern Shore Vacation, you can enjoy it all from the comfort of your very own private chesapeake bay waterfront retreat. Here, where the pace is peaceful and nature abounds, you can experience simple pleasures with family and friends.

Waterfowl Festival
eastern shore fall deals
st michaels rentals

Explore the outdoors—fishing and crabbing, golfing, sailing, swimming, kayaking and biking. Absorb breathtaking views from your secluded dock and relax in your own private pool, instead of lugging your things back and forth to the beach. Stroll our historic and uncrowded scenic streets where you’ll find exquisite fine dining, boutique shopping, and eclectic art galleries.

Each of our charming towns, St. Michaels, Easton, Oxford, Tilghman Island, Cambridge, and Chestertown has its own unique ambiance. Our guests enjoy trying them all!

St. Michaels, MD is best known for it’s nautical ambiance and small town charm. Visitors return for the seafood, shopping and escape from the hustle and bustle. St. Michaels is consistently named as a top vacation destination by travel media.

We offer a spectacular selection of rural waterfront estates, spacious vacation homes and quaint cottages, each meeting the standards and value you’d expect from an Eastern Shore Vacation Home.   And don't forget, most of our homes are dog friendly, so you don't have to leave your best friend behind!

For your next vacation, your picture perfect Chesapeake Bay Vacation Rental awaits!