If you’re curious about the best time to visit the Eastern Shore of Maryland, then you’re in the right place. This page has everything you need to know about each season! Rather than simply tell you which time of year is right for you, we recommend reading about each one and deciding for yourself. That’s because all of the seasons are wonderful opportunities for Eastern Shore vacations! See what sets them all apart and get on the path toward your ideal retreat. Just make sure you explore our incredible collection of rental properties to make the most of your experience here.

Browse Our Properties

Discover the Best Time to Visit the Eastern Shore of Maryland


The spring is a time of renewal and rejuvenation after the cold winter season — both for you as well as nature. And, the Eastern Shore of Maryland is flush with natural scenery to admire. If you’re a nature lover, bird watcher, or outdoorsy person, we highly recommend visiting the Eastern Shore of Maryland in the springtime. Temperatures are mild, and the wildflowers and wildlife wake up from their winter slumber, making it an excellent season to explore the great outdoors.

Springtime Activities:

  • Hiking
  • Biking
  • Bird watching
  • Fishing
  • Picnicking

Springtime Events:


Does the warmer weather appeal more to you? Feel free to plan a visit to the Eastern Shore of Maryland in the summertime! Just keep in mind that temperatures can range from mild to hot, and some days can be very humid. As long as you dress for the occasion, you’re in for a wonderful time! We recommend dressing in layers, drinking plenty of water, and wearing sunscreen on those hot, sunny days. Make sure you plan ahead to join all of the exciting July 4th festivities!

Summertime Activities:

  • Swimming
  • Crabbing
  • Kayaking
  • Paddleboarding
  • Boating

Summertime Events:


Get ready for more mild weather and exciting events once autumn arrives! Fall is a beautiful time of year for your next relaxing retreat on the Eastern Shore of Maryland. Similar to spring, it’s a fantastic chance to head outside, get some fresh air, and marvel at nature’s magnificence. You can even get some healthy exercise in the process as you explore the gorgeous fall foliage! What’s better than that?

Fall Activities:

  • Hiking
  • Biking
  • Hunting
  • Bird watching
  • Picnicking

Fall Events:


It’s time to bring out those warmer clothes and get cozy! Winter might not always seem like the most ideal time for a vacation, but the Eastern Shore will surely change your mind about that. This is the time of year when all of our coastal communities show their true charm via festive events and holiday cheer. All you need is a jacket, hat, gloves, and maybe a scarf to venture out into all of the delightful downtown areas. You’ll love doing your holiday shopping and attending all of the joyous celebrations here!

Wintertime Activities:

  • Shopping
  • Dining
  • Exploring Museums
  • Wine tasting
  • Bird watching

Wintertime Events:

Enjoy Year-Round Getaways With Eastern Shore Vacation Rentals!

The pool outside Cedar Cove on the Miles

Have you decided on your favorite time to visit the Eastern Shore of Maryland? No matter what season you chose, you can enjoy a remarkable getaway with Eastern Shore Vacation Rentals. We are the area’s premier provider of rental homes, cottages, and estates — many of which are directly on the waterfront for gorgeous views and convenient access to your favorite activities. Some of our properties are even pet-friendly, so you never have to leave your furry friend behind on your next vacation!

Browse our properties in the St. Michaels area today, and find your happy place with Eastern Shore Vacation Rentals!

Daily life on the Eastern Shore of Maryland almost always involves two things: water and seafood. Not only is this landmass flanked by the Chesapeake Bay and the Atlantic Ocean, but it’s also filled with intricate waterways that are serene and picturesque. The area’s proximity to fresh and saltwater means there’s always an abundance of delicious seafood to enjoy. And, while the summer is a popular tourist season, winter on the Eastern Shore of Maryland presents its own unique opportunities for a fun-filled Maryland-style getaway. Don’t miss out!

The foundation of any vacation begins with the perfect place to stay. Select one of our Eastern Shore Vacation Rentals to experience the best of Eastern Shore living any time of year. Choose from quaint historic cottages to waterfront homes to luxurious estates.

What Is There to Do in Maryland in the Winter?

The short answer is, a lot! Colder weather means fewer crowds at the top attractions. You can use that to your advantage and book a trip to the Eastern Shore this winter!

1. Explore a Wildlife Refuge

If you love to get outside, no matter the weather, the Eastern Shore of Maryland is a wonderful place to go birding. The Eastern Neck National Wildlife Refuge in Rock Hall offers winter walks in sanctuary areas. Don’t miss the chance to explore areas that aren’t usually open to the public. Keep your binoculars and your camera ready to capture sightings of tundra swans, scaup, Canada geese, ruddy ducks, mallards, buffleheads, and more. You might also see foxes, deer, and groundhogs.

The Blackwater National Wildlife Refuge in Cambridge is another great spot for birding. Look for bald eagles, golden eagles, tundra swans, great horned owls, and a variety of ducks.

2. Eat, Drink, and Be Merry

Easton Shore restaurants understand the best way to capture a traveler’s heart (and keep them coming back) is through an unforgettable meal. As we mentioned earlier, seafood is just about the center of every dish in this area. Try the crab cakes at Theo’s in St. Michaels, baked oysters on the half-shell at Latitude 38 in Oxford, or the oyster stew at Mason’s in Easton.

If you love wine, you’ll enjoy exploring Chesapeake Wine Country. Stop for a tasting at Cascia Vineyards, Triple Creek Winery, and St. Michaels Winery. Don’t forget to pick up something to pair with a delicious meal back home!

3. Holiday Festivities on the Eastern Shore of Maryland

The holidays might be one of the best reasons for a winter trip to the Eastern Shore of Maryland. You’ll get a healthy dose of traditional cheer, plus you can shop for locally made gift items, and sample local delicacies while you’re at it! A few of our favorite Eastern Shore Christmas Events include:

The Eastern Shore Winter Weather Report

Be sure to pack your warm coat, scarf, gloves, and maybe even snow boots if you’re planning a winter getaway. Daily highs range between 39 and 49 degrees Fahrenheit and the National Weather Service keeps us up-to-date on the occasional chance of snow and freezing rain. We think you’ll agree that a little blanket of the white stuff will only further enhance your trip. Imagine waking up one morning to a snow-covered landscape. You’ll have the perfect excuse to stay at your vacation rental all day to sip hot coffee, read, and relax!

Where to Stay in the Winter on the Eastern Shore of Maryland

The best way to enjoy a winter escape to the Eastern Shore of Maryland is to book one of our vacation rental properties. Our large collection of homes, cottages, and estates span St. Michaels, Cambridge, Oxford, Chestertown, and Tilghman Island.  We even have pet-friendly options and last-minute deals!

Browse our seasonal specials and book your ideal vacation rental today! And, check out our events page to discover more celebrations you can enjoy year-round!

The living room inside the Carpenter Alley Cottage

Picture yourself in the great outdoors, surrounded by natural scenery, enjoying your favorite pastime. If your mind went straight to imagining a hunting adventure, then you’re in the right place. Maryland’s Eastern Shore is an incredible destination to make your daydream a reality, and we have all the information you need to make the most of the experience. Read on to see our complete guide to Eastern Shore duck hunting, and browse our collection of vacation rentals to find the ideal property for your trip!

Know Before You Go: Eastern Shore Duck Hunting

Rules and Regulations

Of course, the first thing you need to do is obtain the proper hunting license. Luckily, the Maryland Department of Natural Resources makes it easy — you can even apply for a license online! There are several different options available for both visitors and residents of Maryland’s Eastern Shore. If you’re a non-resident looking to plan a waterfowl-hunting expedition, we recommend the three-day Waterfowl and Small Game License. It only costs $45 and permits you to hunt waterfowl for three consecutive days in season. The duck-hunting season typically takes place in mid-October, late November, and from late December through January.

Popular Spots

The next step is to find the perfect area for your adventure, and the Eastern Shore is overflowing with opportunities. Some of the common duck-hunting destinations in Dorchester include the Blackwater National Wildlife Refuge, Fishing Bay WMA, Tar Bay WMA, and many more. There are simply so many fantastic places for duck hunting on Maryland’s Eastern Shore!

Duck-Hunting Outfitters and Guides

Did you forget your gear at home, or do you feel like picking up some new equipment for your upcoming duck hunt? Don’t worry, because there are several excellent stores that have everything you need. A few of the waterfowl-hunting outfitters and guides we recommend to visitors are Shore Sportsman, Diving Ducks, and Barneck Outfitters, among several others.

Plan Your Hunting Trip With Eastern Shore Vacation Rentals

So, now you know the essential information for an Eastern Shore duck hunting adventure. Are you forgetting anything? You can’t enjoy the ultimate hunting trip without having a fantastic place to stay in the area! Luckily, Eastern Shore Vacation Rentals has you covered with a whole list of properties with luxurious accommodations and impressive amenities. 

Whether you’d like to unwind after your hunt in St. Michaels, Oxford, Cambridge, Tilghman Island, or beyond, we have the perfect property for you. Plus, we have options for everyone from solo travelers to large groups in case you’d like to bring your friends or family along for a hunting getaway.

Don’t delay any longer. Book your favorite property and embark on an Eastern Shore adventure!

The view of Oxford Oasis from the dock

The Eastern Shore of Maryland is a haven for rest, relaxation, and reconnections with nature. Many people visit our beautiful region in the warmer months to immerse themselves in the magnificent scenery with outdoor activities, but our area is spectacular in the winter, too. In fact, it’s one of our favorite times of the year. You might agree with us after you check out these Eastern Shore Christmas events! Plus, you can book one of our vacation rentals to put the icing on top of a magical getaway. It’s the key to unlocking a wealth of holiday cheer!

The Best Eastern Shore Christmas Events


  • Holiday Arts, Crafts & Gifts Fair

Get a head start on your shopping this year with the Annual Holiday Arts, Crafts & Gifts Fair! It takes place in early November with 25 vendors at Emily’s Produce in Cambridge, MD. You’ll find plenty of hand-crafted items that are sure to put a smile on that special someone’s face!

  • Mistletoe Market

Can’t get enough shopping during your vacation? Continue your shopping spree at the Mistletoe Market on Saturday afternoons from mid-November through mid-December at Cannery Way. There’s no shortage of unique gift options here!

  • Winter Wonderland Music and Tree Festival

Get ready for four days of holiday cheer at this year’s Winter Wonderland Music and Tree Festival! There are activities for all ages, including a holiday musical, pictures with Santa Claus, dancing, and more. Don’t forget to bid on a decorated Christmas tree — proceeds benefit the Leukemia and Lymphoma Society of the Eastern Shore.

  • Festival of Wreaths Gala

The Festival of Wreaths Holiday Gala is another excellent event to attend at the beginning of December. You can join the fun at the Pleasant Day Medical Adult Day Care Center in Cambridge for an evening of food, fun, music, and auctions for a good cause.

  • Cambridge Dorchester Christmas Parade

If you can only make it to one holiday event in Cambridge, Maryland, we highly recommend checking out the Cambridge Dorchester Christmas Parade. It’s been an annual tradition for over 70 years! Arrive early on the first Saturday of December to get a good viewing spot as the festive floats, performers, and participants make their way from Long Wharf to Washington Street.

  • Santa Swim

Do you have what it takes to jump into the Choptank River in the middle of the winter? Several brave swimmers take the plunge each year in support of the Care and Share Fund that helps less-fortunate members of the community. You’re welcome to sign up, help raise money, and have a whole lot of fun in the process.

  • Santa Trail Scavenger Hunt

Feel free to test your treasure-hunting skills toward the end of December in Downtown Cambridge! The Santa Trail Scavenger Hunt is the ideal Christmas activity for families looking to explore the area and pick up treats at a variety of local businesses. Can you solve all the clues and find Santa’s secret location?


  • RiverArts Holiday Show and Gift Sale

No matter who’s on your shopping list this season, you can find the perfect presents at the Chestertown RiverArts Holiday Show and Gift Sale. There’s a wide variety of items to choose from, and the market runs from late November all the way through late December. 

  • Dickens of a Christmas Weekend

Take a journey back in time for a Victorian celebration this December! Dickens of a Christmas is Downtown Cambridge’s premier holiday event that spans three days with historic house tours, fashion shows, bonfires, live performances, and so much more.


  • Festival of Trees

‘Tis the season of giving, and there’s no better feeling than giving to an honorable cause. The Festival of Trees in Easton is a fantastic opportunity to do that. There’s so much fun to be had here, including the new addition, Carols by Candlelight. Proceeds go toward helping terminally ill patients at Talbot Hospice.

  • Moonlight Madness

Did you know that you earn raffle tickets just for shopping at participating local businesses in Easton from November to the beginning of December? It’s true! And, you get a chance to win $10,000 worth of prizes during the drawing at Moonlight Madness. It’s an evening of late-night shopping, celebrating, photographs with Santa, and even free carriage rides through town!

  • Holiday Parade

Of course, you can expect plenty of remarkable parades during Christmas time on the Eastern Shore of Maryland. Easton, MD, is no exception! Check out the annual Holiday Parade in early December to get in the spirit of the season with a tree lighting and a one-mile parade throughout the downtown area. 

St. Michaels

  • Midnight Madness

Easton has Moonlight Madness, but it’s not to be confused with Midnight Madness in St. Michaels, Maryland. Shops remain open until midnight, as you might expect from the event name, providing extra hours of holiday cheer and fun for visitors. You can even score some exclusive deals and win more raffle prizes!

  • Christmas in St. Michaels

Make sure you don’t miss out on Christmas in St. Michaels, a must-see festival with holiday activities during three fun-filled days in mid-December. Some of the events include a gingerbread house competition, yuletide party, Breakfast with Santa, Santa’s Wonderland, and more. Don’t forget to purchase your souvenir ornament — there’s a different one each year to collect!


  • Christmas on the Creek

Christmas on the Creek is another excellent, multi-day festival that takes place in the quiet town of Oxford, Maryland. Expect plenty of fun things to do for the whole family, including the annual tree lighting and a Christmas bazaar.

Reserve Your Vacation Rental for the Holidays!

Do you know what makes these Eastern Shore Christmas events even more special? We offer beautiful properties near them all! Eastern Shore Vacation Rentals has an extensive collection of homes, cottages, and estates in each of these charming towns. Whether you’re looking to celebrate the holidays in St. Michaels, Cambridge, Oxford, Chestertown, or even Tilghman Island, we have the ideal property for you. Some of them are even pet-friendly, so you can spend this special season with the whole family, including your furry, four-legged pals.

Browse our seasonal specials and book your ideal vacation rental today! And, check out our events page to discover more celebrations you can enjoy year-round!

The living room inside Sycamore Acres

One of the top reasons that people visit Maryland’s Eastern Shore is to unwind, enjoy some fresh air, and immerse themselves in the undisturbed beauty of nature. If this sounds like something you’re interested in, there’s one place you don’t want to miss. It’s the Blackwater National Wildlife Refuge in Maryland! This 28,000-acre space is a year-round paradise for animals and animal lovers alike in Dorchester County near Cambridge. Check out our guide to it all and embark on a scenic adventure! Just don’t forget to browse our list of vacation rentals so that you have a place to relax and rest your legs after your fun-filled day at the refuge.

Explore the Blackwater National Wildlife Refuge in Maryland


Are you hoping to catch a glimpse of some rare and beautiful birds? If so, you’ll be happy to know that birdwatching is one of the most popular activities at the Blackwater National Wildlife Refuge. Consider visiting between November and February for the best chance at spotting a variety of waterfowl, including swans, geese, and over 20 different species of ducks along the walking trails. Make sure you keep an eye out for osprey, great blue heron, and bald eagles as well!

Local tip: Would you rather admire the wildlife from your automobile rather than trek through the trails? Feel free to take advantage of the Wildlife Drive and enjoy three miles of scenery from the comfort of your car!


In addition to the four hiking trails, there are also three water trails for canoeing and kayaking at the Blackwater National Wildlife Refuge. Feel free to bring your boat along on your getaway and paddle your way through nature’s magnificence on the Purple Trail, Orange Trail, and Green Trail. There’s even an interactive paddling map for your phone to help make sure you make the most of your journey on the water!

Fishing and Hunting

Get ready to reel in some lasting memories! You’re welcome to go fishing and hunting at the Blackwater National Wildlife Refuge as long as you obtain the proper licenses and abide by all rules and regulations. Anglers can cast their line and try their luck with largemouth bass, striped bass, catfish, perch, and more. If hunting is more your style, you can expect to see plenty of deer, turkey, and waterfowl.

Local tip: Bring your kids to the refuge on the first Saturday of June to enjoy the Youth Fishing Fun Day! It’s an opportunity to spend quality time together in the great outdoors with free equipment, food, and prizes.

Plan Your Visit!

Now that you know all about the Blackwater National Wildlife Refuge, it’s time to check it out for yourself! Luckily, Eastern Shore Vacation Rentals has you covered with a wide variety of properties available nearby, including several rentals in Cambridge, MD. Whether you’re looking for a cozy cottage on the shoreline or a sprawling estate with a pool and plenty of amenities, we have the perfect option for you. Plus, we go far beyond simply providing you with a place to stay. All of our properties come with superb customer service to help you plan the perfect getaway as well as seasonal specials to make the most of your experience here.

Browse our collection of beautiful properties today and get one step closer to an unforgettable vacation!

An aerial view of Bayberry Cove in Cambridge, MD

If you’re searching for unspoiled natural beauty and fresh seafood on the Chesapeake Bay, you go to Tilghman Island. And, if you’re looking to celebrate everything that makes this destination special, you attend the Tilghman Island Day Festival! This exciting event takes place every October with great food and fun activities for all ages. Find out why you don’t want to miss it this year. And, browse our selection of Tilghman Island vacation rentals to make sure you have a fantastic place to stay near the celebration!

Top 3 Reasons to Enjoy Tilghman Island Day


Of course, you can expect any event here to include fresh, delicious seafood, and Tilghman Island Day is no exception. Remember to bring your appetite for boat-to-table delicacies like raw or steamed oysters, oyster stew, crabcakes, and so much more. Even if you don’t like seafood, you’re sure to find something to please your palate. Chefs and food vendors also serve up several classic options, including hot dogs, hamburgers, and barbecue chicken. 

Tip: Don’t forget to browse the nautical-themed crafts from local artisans, too! There are plenty of wares available that make ideal gifts or souvenirs to remember your visit to Maryland’s Eastern Shore.


Don’t fill up too much or spend all your time indulging in the food. (Although, we know it’s difficult to tear yourself away from all the enticing options!) You’ll also want to participate, or at least spectate, the variety of fun activities and events. Here are a few of the many options to look forward to this year:

  • Boat Docking Contest
  • Rowboat Race
  • Anchor Throw
  • Oyster Shucking Contest


One of the best reasons to visit Tilghman Island is the sense of community that this small fishing village offers. The Tilghman Island Day Festival isn’t only an excellent opportunity to spend time with the current friends and family members with you. It’s also a chance to meet new people and share lasting memories with them!

Visitor Info

  • Tickets are $5 per person.
  • The festival occurs from 10:00 a.m. to 5:00 p.m.
  • Don’t forget to attend the Tilghman Island Crab Fest in July for more food and fun!

Plan Your Trip With Eastern Shore Vacation Rentals!

Are you ready to experience the excitement of the Tilghman Island Day Festival on the Eastern Shore of Maryland? It’s worth checking out our selection of properties and vacation spots nearby, even if you’re only considering the idea of a getaway. You can secure a rental in the heart of the action with our Tilghman Island properties or unwind in a quiet retreat a little further away in the St. Michaels area and drive to the event. Either way, we’ll make sure your experience is flawless. Browse our entire list of Eastern Shore properties today to get started!

The living space inside the Clearview property on Tilghman Island

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

Sometimes, simply thinking about Cambridge might send you into a state of serenity. It’s a paradise for family vacations where you can stroll through the downtown area, explore the town’s history, soak up the waterfront views, and set sail on scenic cruises. While it’s a fantastic destination for relaxing retreats, this community on Maryland’s Eastern Shore sure knows how to celebrate, too! Feel free to jump into all the excitement — we made a convenient guide for some of the top annual events in Cambridge, MD, to make sure you never miss out. Plus, you can enhance your experience further when you reserve one of our beautiful vacation rentals in the area!

Discover the Best Cambridge, MD, Events


There’s always something fun going on in Cambridge during the summertime, from the fireworks over the Choptank River to fun-filled festivals. When you’re not sunbathing and barbecuing with the family, feel free to check out some of the hottest events of the summer:

  • Independence Day Fireworks
  • Taste of Cambridge: Crab Cook-off 
  • Seafood Feast-I-Val
  • Light Night Cambridge!
  • GrooveFEST
  • Showcase Art Walk and Street Festival


There may not be as many festivals as the summertime, but you’re sure to fall in love with Cambridge when you attend these events. One of the biggest events of the season, and possibly the entire year, is the annual IRONMAN Maryland triathlon. It’s an opportunity to swim, bike, and run through our incredibly scenic region. You’ll get some exercise and have plenty of fun in the process! Here’s a taste of what to expect each fall in Cambridge, MD:

  • IRONMAN Maryland
  • Crabtoberfest


Happy holidays! When winter arrives, so does the holiday cheer. And, the local community loves to show off its holiday spirit with a variety of festivities. Feel free to check out these winter events in Cambridge, MD, and don’t forget to get some holiday shopping done in the downtown area. You can even warm up with a delicious meal and some hot cocoa at a cafe or restaurant.

  • Christmas Train Garden
  • Christmas Parade
  • Santa Swim


Spring back into the excitement and enjoy the beauty of springtime with wine, flowers, boating, and more! It’s already one of the best times to visit Maryland’s Eastern Shore, and the local events can make your vacation even more memorable. These are just some of the many ways to make it happen each spring:

  • Downtown Cambridge Wine Festival
  • St. Paul’s Flower Fair
  • Cambridge Classic Power Boat Regatta

Find Lodging for Your Favorite Celebrations!

It can be difficult to choose between all of these must-see events. Once you narrow your search down to your favorites, we’d love to help you select the best lodging option in the area for them. Whether you’d like to stay in the heart of the excitement or secure a relaxing escape a little further away, we have the ideal property for you. Eastern Shore Vacation Rentals is the premier property rental company in the area — and for several good reasons! 

Explore our list of Cambridge vacation rentals to take the next step toward paradise. Just don’t forget to check out our specials and book direct for the best deal. See you on the Eastern Shore this year!

The view of Indian Fields from the yard

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

This is where your adventure on the water begins! We’ve got all the information you need about the top companies for boat rentals in Annapolis, MD. Discover the possibilities and get one step closer to the beauty of the Chesapeake Bay. By the time you get back to shore, you’ll have memories to last a lifetime. Just make sure there’s a beautiful vacation rental waiting for you back on land. Browse our selection of properties in Annapolis and find the ideal retreat for your next getaway!

Annapolis Electric Boat Rentals

There are no surprises here — this company has you covered with electric boat rentals in Annapolis! Their 22-foot long boats are perfect if you’re looking to slow things down, enjoy the scenery, and spend quality time with your friends and family. The boats are easy to handle, but AEBR goes the extra mile by providing in-depth instruction to make sure you feel completely comfortable driving it. Plus, the canopy on top of each boat provides some pleasant shade during those hot, sunny days on the water.

South River Boat Rentals

Another fantastic option is South River Boat Rentals in nearby Edgewater, MD. They offer 25 different boats to choose from with round-the-clock service available. Whether you’re looking to go sailing, fishing, or celebrate a special occasion on a luxury yacht, they’ve got you covered. They even provide gear if you’d like to try some fun watersports!

Paddle or Pedal

Paddle or Pedal has everything you need for adventures by land and by sea all in one convenient place. Check out their Annapolis location, Quiet Waters Park, to pick out your favorite pedal boat, sailboat, kayak, canoe, bicycle, and more. They have flexible rental options and convenient lessons available, too!

The List Goes On!

The options for charters and boat rentals in Annapolis, MD, don’t stop there. If you haven’t found what you’re looking for yet, consider checking out some of these great companies in the area:

  • Kayak Annapolis
  • Annapolis Canoe and Kayak
  • Dream Yacht Charter
  • Classic Sail Charters
  • Cruise Annapolis
  • Dancer Sportfishing Charters

Find the Perfect Vacation Rental for Your Visit to Annapolis

There’s nothing better than spending a day out on the water, then returning for an evening of luxury inside a beautiful vacation home. It’s not a daydream — it’s a reality with Eastern Shore Vacation Rentals! We have options for every budget and all group sizes in Annapolis, Maryland. Plus, we’re always adding more! Head over to our properties page to view the possibilities and make your dream vacation come true. Just don’t forget to book direct and browse our list of current specials to get the best deal on your stay!

Nantucket on the Chesapeake