Holidays & Events

Winefest at St. Michaels

A not to miss premier international wine tasting event set in our charming town of St. Michaels, WineFest is a popular weekend to visit the Eastern Shore to savor wine and local cuisine and catch your first breath of spring!

April 28-29, 2018
For more information:

Oxford Day

A fun weekend to celebrate all things Oxford! Ice Cream, the Ferry, a Parade and more make this a great family (and doggie!) friendly event.

Memorial Day Weekend

Join us for the unofficial start of summer! Summer was a long time coming and we can't wait to launch the boats, steam the crabs, fire up the grills. Don't wait too long--this popular weekend sells out quickly! Please note there is a three night minimum stay for Memorial Day Weekend.

Sail Into Spring Specials

ASpring getaway to the Eastern Shore is just what the doctor ordered to dust off the cobwebs from a long, long winter! Whether you are looking for a home base to explore the area, a cottage to relax and unwind in, a pet-friendly property or a place to get active, there are many great options. Now is the time to book your Spring vacation and save 20% on a 3+ night stay! Bed and bath linens and home amenities are included so all you need to do is pack. Hope to see you soon on MD's Eastern Shore!

July 4th Holiday

Celebrate the 4th the Eastern Shore way! Waterfront fireworks, crabs and cold beverages, old-fashioned carnivals and parades for the kids and big band night for the grown-ups. One of the best times of the year to visit!

Star World Championship

Coming to Oxford for the Star World Championships? Use code STAR receive 15% off during your stay in participating properties.

Thanksgiving on the Shore

Thanksgiving is a special time to visit MD's Eastern Shore--beautiful colors, waterfowl migrating above, succulent seafood (oysters!!) and local cuisine all set a perfect backdrop for a treasured family celebration. There is a 3-night minimum stay requirement for the Thanksgiving holiday weekend. Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

New Years Eve

The Eastern Shore is a fun, low key place to ring in the New Year! Great restaurants, charming family-oriented activities such as First Night Talbot in Easton (complete with Crab Drop!) and cozy cottages to spend time with those that matter most.

Waterfowl Festival Weekend

The Eastern Shore's signature annual event, the Waterfowl Festival is an event packed family weekend for celebrating all things Eastern Shore--food, fowl, and fun! For more information, visit

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