This Easter, start a new family tradition with a weekend on Maryland’s serene, historic Eastern Shore. 

Grab your basket and hunt for eggs amid breathtaking waterfront vistas. Explore local waterways by kayak and ride bikes into the towns where life moves at a slower pace. When it’s time for your big holiday meal, prepare ham, lamb or a steaming pot of crabs in a kitchen stocked with everything you need. 

Eastern Shore Vacation Rentals has a selection of properties just right for your family or several families. Dogs are welcome, at no extra charge. And all ESVR properties include bed and bath linens, with beds made prior to your arrival. 

Find your favorite and book now for Easter weekend before they’re gone.

Cozy and Charming Homes

Treat your family to the quintessential Eastern Shore experience in one of our quaint cottages. Beautifully appointed and picturesque, each home allows you to feel more connected but never cramped.

Mallard Point Cottage – SOLD OUT!

McDaniel, MD 

4 Bedrooms 3 Baths Sleeps 8

Share laughs and stories together on Mallard Point’s large screened-in porch looking out to the water. Feel the stress melt away with coffee or cocktails on your private dock. And spend evenings snuggled up with a book or watching movies by the crackling fire.

Caulk’s Cove

Bozman, MD

3 Bedrooms 2.5 Baths Sleeps 6

Find total relaxation just outside the historic water town of St. Michaels. Caulk’s Cove is a secluded paradise with everything your family needs to make a memorable Easter, including a deep-water pier and an outdoor fire pit. Toasted Peeps, anyone?

Pride and Joy

Oxford, MD

3 Bedrooms 2 Baths Sleeps 6

The brick walkway, lush landscaping, white picket fence and screened porch tell you all you need to know about this gorgeous cottage. It’s a slice of small-town Americana, decorated with bright colors throughout and furnished for comfort. You’re just a short walk from Oxford’s parks and unique restaurants.

Multi-Family Rentals

When it comes to the holidays, the more the merrier. These sprawling estates have more than enough room for your extended family or several other families to join the Easter festivities.

Willoughby – SOLD OUT!

Cambridge, MD

7 Bedrooms 6 Baths Sleeps 24

This retreat on the Hudson Creek waterfront redefines the term living large. The inside includes more than 10,000 square feet of luxurious amenities and furnishings you have to see to appreciate. The heated indoor pool and screened-in hot tub are both open for use year-round.

Belle Aire Landing

East New Market, MD

9 Bedrooms 6 Baths Sleeps 22

A private beach on the Choptank River. A dance hall converted into a guest house. Waterfront dining. A waterside crab house. Exquisite furnishings and details throughout. This compound near Cambridge has all you could ever want and need for an incomparable Easter holiday.

Time to explore

You may not wish to leave your rental property, but if you do, Maryland’s Eastern Shore has a bounty of attractions for families. 

In Cambridge, the Harriet Tubman Underground Railroad Visitor Center and State Park gives you a close look at the incredible life and brave deeds of a true American hero.  

Kids of all ages love the Chesapeake Bay Maritime Museum in St. Michaels, where you can tour a working shipyard, see a lighthouse from 1879, join the crew of an oyster harvesting skipjack and try your luck harvesting crabs and other seafood. If you come down to celebrate Easter a week early, be sure to visit the 9th Annual Eastern Shore Sea Glass and Coastal Arts Festival on April 4 and 5. 

Easter weekend is nearly a month into spring, so take advantage of favorable April weather with a trip to the Blackwater National Wildlife Refuge. There’s a guided birding tour on Saturday, April 11, where you’ll have a chance to see bald eagles and several species of waterfowl.

Plan your new Easter tradition with ESVR

Pack up your baskets, bonnets and chocolate bunnies this Easter and treat your family to an unforgettable holiday on Maryland’s Eastern Shore. 

Whether you need to accommodate one family or five, ESVR has the home to make your trip special. Find and book your favorite rental through ESVR to avoid extra fees. If you have any questions about Easter weekend or anything else, reach out to our reservations team at 410-770-9093 or [email protected].

Historically known as “The Town that Fooled the British,” St. Michaels, MD is the most popular destination in our collection of waterfront towns. Offering a variety of activities, shops, and restaurants, there are countless attractions and things to do in St. Michaels for everyone in the family to enjoy.

Things to Do in St. Michaels, Maryland

1. Visit the Chesapeake Bay Maritime Museum

The Chesapeake Bay Maritime Museum is in the center of St. Michaels and offers visitors a chance to learn about the heritage of the Chesapeake Bay. The waterfront campus includes interactive exhibitions, tours, and scenic boat rides, demonstrations, hands-on education programs for children and adults, and annual festivals that celebrate the Chesapeake Bay culture.

During the year, there are several fun events hosted by the Museum to enjoy–OysterFest in October, July 4 fireworks, the Charity Boat Auction, Big Band Night and Waterman’s Appreciation Day are all local and guest favorites.

2. Discover Kid-friendly Things to Do in St. Michaels

The best part about this community are the variety of kid-friendly things to do in St. Michaels! Kids love the opportunity to: tour a real lighthouse, and the Chesapeake Bay Maritime Museum also offers family sleepovers for children to experience the life of a lighthouse keeper.

3. Check out The Historic Mill Complex

The Historic Mill Complex is an industrial hip-chic atmosphere and features a winery, brewery, and distillery. Spend some time tasting local wines, enjoying some spirits and learning about the beer-making process.

4. Enjoy a Wide Variety of Dining Option

There is a fantastic array of restaurants in St. Michaels, and you are in for a treat as you stroll along the charming town. From waterfront crab houses where you can learn to pick crabs and enjoy the best local seafood while taking in bay breezes and scenic water views, to upscale restaurants with fine dining for a special evening out, you will want to bring your appetite along. Some of our favorites include:

  • Limoncello for authentic Italian cuisine
  • Ava’s for delicious wood-fired pizza
  • Theo’s Steak House, for an upscale steakhouse experience
  • St. Michaels Crab & Steak. The Crab Claw is a local icon offering an authentic crab house experience overlooking the harbor.
  • Justine’s for a sweet treat. This is a local favorite for ice cream
  • Gina’s Bakery for homemade goodies perfect to take home to enjoy along with your morning cup of coffee.

5. Get On the Water

Want to get on the water? There are many water activities and things to do outdoors in St. Michaels. Take a boat ride or charter, or for the more active vacationer, you can rent kayaks or paddleboards. A guest favorite is the H.M. Krentz, a working skipjack offering daily tours to learn about oyster dredging and local history and experience the life of a waterman by helping pull up sails. The Patriot offers narrated cruises aboard a replica of a 1930’s steam ferry, or for an upscale sailing experience, the Selina II is perfect for an intimate sunset cruise. Shore Pedal and Paddle has an array of kayaks and paddleboards for you take out or stop by the Maritime Museum to rent a boat there.

6. Rent a Bike and Explore

Biking is very popular in St. Michaels whether you’d like to just explore the town at a slow pace or take on a more ambitious ride along some of our scenic bicycle trails. Several shops offer bike rentals for all ages and levels of experience.

7. Spend the Day Shopping

The historic district of St. Michaels is also home to some of the best shopping around! You can find a keepsake treasure in the local antique shops, browse the many upscale boutiques, discover a new favorite artist in one of the eclectic art galleries or get some inspiration for your home by visiting some of the furniture and accessories shops. Kids love the candy and Christmas shops, as well as the souvenir stores (crab hats, anyone?) to find that perfect keepsake for your visit.

8. Experience the Offseason

An offseason trip to St. Michaels will not disappoint. Starting in October, St. Michaels hosts a variety of fall events where you can enjoy the cooler temperatures, beautiful foliage and seasonal delicacies such as oysters and crab soup. Fall into St. Michaels weekend in October is a family-friendly event or be sure to visit for Oysterfest for great seafood, music, and local flavor.

St. Michaels is one of the best Christmas destinations on the East Coast. The town pulls out all of the stops with spectacular holiday decorations, parades, homes tours and more.

Book Your Next St. Michaels vacation with Eastern Shore Vacation Rentals

Eastern Shore Vacation Rentals is proud to offer a variety of St. Michaels Vacation Rentals for your next visit. Browse and book these beautiful properties today!

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