Living Like a Local on MDs Eastern Shore

You've found the perfect house, now let us help you plan your perfect vacation!  From fabulous food to experiencing bay breezes out on the water, biking and kayaking, shopping or history, there is something for everyone. There are so many different ways to enjoy the Eastern Shore, tell us what you like to do on vacation and we can point you in the right direction!

Golf Anyone?

Golf Anyone?

Maryland`s Eastern Shore is home to several excellent public courses, ranging from nationally top rated to scenic waterfront courses to satisfy any golf enthusiast.

You, the Athlete

You, the Athlete

The Eastern Shore is the ideal place to take your fitness goals to the next level. Scenic biking and running trails are plenty or partake in one of the many organized rides or runs throughout the year.

Restaurants of the Eastern Shore

Restaurants of the Eastern Shore

It`s all about the food! Here are some of our suggestions to soak up some unique local flavor.

You, and your Dog

You, and your Dog

If taking a vacation without your best friend doesn`t sound like much of a vacation, you`re in luck! Most ESVR properties are dog-friendly, and we do not charge additional fees to bring your dog along! Please note there is a two dog limit.

The Eastern Shore is very pet-friendly! Here are some fun things to do with your best friend while staying in the area. Browse our pet-friendly homes to start planning your trip today!

You, on the Water

You, on the Water

Your vacation isn`t complete without spending some time on the glistening water of the Chesapeake Bay. These Eastern Shore watersports are some of the best ways to do it! Check out our local tips on boat charters, marinas, jet ski rentals, and more so you can explore the Bay like a pro. Then, find your ideal property and get one step closer to enjoying all of these exciting Eastern Shore activities on the water. We have a wide variety of vacation rentals to help you explore the beauty of the Bay!

Make a Splash With These Eastern Shore Watersports

You, the Artist

You, the Artist

Discover why artists come from all over the world to showcase their art and be inspired to create. Whether taking in a gallery or museum, shopping for local artisan jewelry and other handmade items, or enjoying a show at our classic Avalon Theatre, there`s plenty to nurture your creative side!

You, the Foodie

You, the Foodie

When making your packing list for your Eastern Shore vacation, be sure to bring your appetite! We have an amazing array of restaurants, from casual local specialties to world-class fine dining.

Enjoy fresh local seafood, fruits, and vegetables in the summer as well as our famous ice cream (voted one of the Best in the Country!), or plan a winter destination to enjoy a cozy gourmet meal. Whatever the time of year, you will not leave disappointed or hungry!

You, the Historian

You, the Historian

Our area is rich in history and tradition. Be sure to spend some time at our museums to learn about Eastern Shore Heritage.

You, the Sportsman

You, the Sportsman

The Eastern Shore of Maryland has a longstanding tradition of outdoor sporting. Something is always in season on the shore! Whether you are interested in hunting, fishing or crabbing, we can help you find the resources you need to enjoy the wild side of the Eastern Shore! There are abundant guides, charters, and other opportunities to land the "big one" or just have a little bonding time with the grandkids crabbing off the dock.

You, With Kids

You, With Kids

Keeping the kids entertained on the Eastern Shore is easy! Our picturesque atmosphere is perfect for getting out and exploring nature together. Some of the best Eastern Shore family-friendly activities include crabbing, hiking nature trails, sailing, kayaking, and so much more. Not only will you all get some healthy fresh air, but you’ll be making lasting memories in the process. After your adventures, treat the little ones to sundaes at our local ice cream shops! The first step is to book your vacation rental, and we have plenty of properties to suit the entire family, no matter how big or small. Take a look and surprise the family with an Eastern Shore vacation this year!

The Best Eastern Shore Family-Friendly Activities