5 of the Best Eastern Shore Vacation Spots

St Michaels Harbor at Sunset

Are you headed toward Maryland’s Eastern Shore this year? You’re already on the right track! It’s an incredibly beautiful and scenic area of the country with several different communities to visit. Luckily, we made a guide to help you decide between the top five Eastern Shore Vacation Spots. All you need to do is take a quick look and find your ideal destination. And, of course, reserve the perfect vacation rental in your chosen location. You’re in luck, again, because we’re the area’s premier boutique vacation rental provider with properties in all these remarkable communities!

Which Eastern Shore Vacation Spot Is Right for You?

St. Michaels

The view from the lawn and gardens of Osprey Point in St. Michaels, MD

Of course, you have St. Michaels in the heart of it all with a bustling historic district, beautiful homes, and upscale vacation vibes. Simply park your car and explore the charming streets that are lined with shops, restaurants, and museums. You’re also welcome to set sail on a number of boat tours from the several marinas. Make sure you save plenty of time to walk through the Chesapeake Bay Maritime Museum!

Fun fact: Did you know that the famous and successful movie, The Wedding Crashers, was filmed in St. Michaels?


An aerial view of Hudson Manor in Cambridge, MD

If you plan on visiting Cambridge, you’re in for another treat. This lovely and scenic community allows you to rent a large group or multi-family home to enjoy a destination in itself. There are 1,700 miles of shoreline, and we have beautiful cottages all along the way. Several of them have private piers where you can dip your toes in the water, fish for a variety of species, or simply enjoy the waterfront views. If you love animals and enjoy birdwatching, make sure you check out the Blackwater National Wildlife Refuge in the area.


The front view of the Thornton building in the fall

We also have a variety of properties in the Chestertown and Centreville areas, offering you quiet retreats near all the brick-lined sidewalks and charming neighborhoods. This community is ideal for relaxation and rejuvenation, but it’s also close enough to the Bay Bridge and several different fun attractions on the Eastern Shore of Maryland. If you’re headed in this direction, we recommend taking a stroll down the historic district to admire the architecture. Foodies will especially enjoy the series of local farmers markets and the variety of farm-to-table restaurants.


The front view of the Thornton building in Chestertown, MD, in the fall

Discover the true meanings of relaxation and serenity when you visit Oxford. This quiet, sleepy, small town on the Eastern Shore of MD is ideal for people who enjoy leisurely days on the waterfront. Consider renting a cozy cottage by the shoreline. You can park your car at a beautiful vacation rental and just walk to all of your favorite shops, restaurants, and fishing spots. Oxford, MD, is still somewhat of a hidden gem, meaning you won’t get a lot of the crowds that other destinations on the Eastern Shore of Maryland can attract during peak season.

Tilghman Island

The front view of Simplicity Cottage in Tilghman Island, MD

If you’re looking for another quiet, off-the-beaten-path vacation destination that’s still close enough to the charm of St. Michaels, consider a trip to Tilghman Island. It’s a charming, quaint, fishing village with a wealth of unspoiled natural beauty. If you love seafood and sailing, this is the Eastern Shore vacation spot for you. Feel free to unwind in the comfort of your property or journey out onto the Chesapeake Bay on a variety of boat charters and tours. Afterward, satisfy your hunger with the excellent restaurants in Tilghman Island and St. Michaels nearby!

Enjoy Your Favorite With Eastern Shore Vacation Rentals

Words can’t possibly do these Eastern Shore vacation spots any justice. So, that means you need to come on down and experience them for yourself! Hopefully, we helped you find your ideal community to use that PTO and treat yourself to some well-deserved relaxation.

Whether you’re leaning toward St. Michaels, Cambridge, Chestertown, Oxford, or Tilghman Island, your perfect getaway is just a click away. With our wide variety of properties, all-inclusive pricing, best price guarantee, and no pet fees, there’s no better company to trust with your trip than Eastern Shore Vacation Rentals. Why would you stay at a drab hotel on the Eastern Shore of Maryland when you can enjoy one of our stunning properties?

Browse our properties now, and get one step closer to the vacation of your dreams! Just don’t forget to browse our current specials and book direct on our website to secure the best deal on your trip.

The living room inside the Carpenter Alley unit