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What Are the Best Things to Do on Kent Island, MD?

Natural beauty and memorable activities await you on Kent Island! One of its many claims to fame is that it’s the largest island in the entire Chesapeake Bay, stretching from Kent Point in the south to Love Point in the north. That means there’s plenty of room for you to enjoy all of the things to do on Kent Island, MD! And, trust us, it’s a worthwhile day-trip destination from our properties along the Eastern Shore of Maryland. If you haven’t done so already, check out all of the beautiful vacation rentals we have waiting for you in the St. Michaels, Oxford, Cambridge, Annapolis, and more!

4 of the Best Things to Do on Kent Island, MD

Enjoy the Scenery

Whether you prefer to walk, run, bike, or simply sit back and admire the views, there are so many opportunities to get out and explore the natural beauty of Kent Island. You can venture through a variety of trails like the Cross Island Trail and South Island Trail in Stevensville. Or, feel free to plan a relaxing day at the shore with scenic destinations like Matapeake Beach and Terrapin Beach Nature Park. Keep an eye out for some fascinating wildlife species, especially if you’re an avid bird watcher!

Browse Shops

Who doesn’t love checking out unique stores and boutiques? Make sure you save plenty of time for shopping on Kent Island, even if you just plan on window shopping. The downtown Stevensville area is perfect for when you want to spend a delightful afternoon searching for gifts, souvenirs, or home decor. One of the highlights here is Stevensville Antiques, where you can discover a variety of charming treasures!

Grab a Bite

Don’t worry when hunger strikes after all your outdoor adventures and shopping trips. There are so many excellent restaurants on Kent Island, MD! Of course, you might not be surprised to find out that the specialty is usually seafood due to all of the marinas and thriving fishing industry on the island. If you’d rather grab a drink rather than a full meal, you’re in luck there as well! There are plenty of Kent Island bars to check out, like the Pour House Pub on the northern end of the island and Dirty Dave’s Tiki Bar toward the southern side.

Explore History

Did you know that Kent Island was the first permanent English settlement in Maryland? That means we have good news for all of you history buffs out there. There are several must-see historical sites throughout the area. Feel free to visit the Stevensville Train Depot which dates back to 1902 and marvel at any of the historic buildings throughout Stevensville Arts and Entertainment District.

Enjoy Them All During Your Eastern Shore Vacation

Don’t simply read about this incredible place — get out there and start enjoying everything it has to offer! Eastern Shore Vacation Rentals has a wide variety of beautiful properties from the St. Michaels area to Annapolis, which are both within driving distance of Kent Island via the Kent Narrows Bridge or the Chesapeake Bay Bridge. You’ll love spending a fun-filled day on the island, then being able to head back to a stunning waterfront home, cottage, or estate. It’s not a daydream. It’s a reality, and we invite you to take the first step today. 

Browse our properties and find your happy place now!

The living room inside Fleet Street
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5 of the Best Eastern Shore Vacation Spots

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?

Cambridge

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.

Chestertown

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.

Oxford

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
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