The Eastern Shore has something for everyone, whether you’d like to set sail, cast a line, or just kick back and relax. The possibilities are endless! Start planning your dream vacation with our guide to the best attractions on the Eastern Shore of Maryland. Before you know it, you’ll have a full itinerary of activities and restaurants to try. The next step is experiencing them all, and we can help with that, too! Browse our boutique selection of cottages, waterfront homes, and estates and take the next step toward the scenery and serenity of the Eastern Shore!

In addition to the resoures below, you can also learn more about upcoming events and things to do by reading our blog.

Check Our Our Blog

Your Guide to the Best Things to Do on Maryland’s Eastern Shore

Plate of delicious gourmet food

Foodies

When packing for your Eastern Shore vacation, don’t forget to bring your appetite! Our area is full of local seafood restaurants and farm-to-table eateries to satisfy any craving. Stop in at one of our favorites and try the fresh catch of the day!

Indulge

Family kayaking on the ocean

Seafarers

The gorgeous coastline of the Chesapeake Bay isn’t just for looking at. Grab a paddle and venture onto the shimmering seas! Learn where to rent kayaks, jet skis, paddleboards, and more. Or, sign up for a sunset cruise and tour the coast in style.

Set Sail

Bushel of blue crabs

Adventurers

Whether you’re a seasoned sportsman or you’re just learning the ropes, we can help you enjoy the great outdoors. The Eastern Shore is perfect for hunting, fishing, and crabbing, so there’s always something in season!
 
Embark

Feet on bycikle pedal in sunset light - close up image

Fitness Fans

Don’t let a vacation stop you from achieving your fitness goals! Maryland’s Eastern Shore has a variety of scenic hiking and biking trails to explore. Rent a bicycle and enjoy a leisurely ride or sign up for an endurance event to challenge yourself.

Exercise

Art Gallery

Artists

Nurture your creative side by visiting our many art galleries and museums! Showcase events such as the Waterfowl Festival and Plein Air Easton will inspire the artist in anyone. Purchase your favorite works and take home unique souvenirs!
 
Inspire Yourself

family holding hands on a beach

Families

If you’re traveling with kids, you won’t have any problem keeping them entertained here. Our family-friendly destination has everything they could want, from parks and playgrounds to ice cream shops and toy stores.
 
Vacation Together

Corgi running on beach dog

Dog Lovers

Dogs love vacations, too! You don’t need to leave your loyal pal behind when you choose Eastern Shore Vacation Rentals. We have over 60 beautiful properties, and most of them are pet-friendly with no extra fees! (Two-dog limit, please)

Woof!

paper wisdom, old books, old legal books

History Buffs

There’s no shortage of fascinating places to visit on the Eastern Shore of MD. Take your mind on an adventure as you explore museums and historic sites. You might learn a spooky ghost story along the way!
 
Learn

Happy friends taking selfie with smartphone at beach party outdoor - Young people having fun at kiosk bar drinking champagne - Soft focus on mobile cell phone - Youth lifestyle and vacation

Friends

Are you planning a getaway to reconnect with old friends? Create lasting memories together at our local shops, spas, golf courses, and more! Maryland’s Eastern Shore towns are full of fun group activities to enjoy.
 
Make Memories

Enjoy It All With Eastern Shore Vacation Rentals!

Have you picked your favorites? Now, it’s time to experience them! Just like how the Eastern Shore of Maryland has attractions for everyone, we have vacation rentals for everyone. Our portfolio of boutique properties includes cottages, waterfront homes, and picturesque estates. We’re the perfect alternative to Maryland’s Eastern Shore hotels, letting you and your travel companions stretch out and relax at your own private retreat. We have options in St. Michaels, Oxford, Tilghman Island, and beyond!

Find your happy place today. Your future self thanks you!