Best Maryland Vacations

Welcome to our guide to Maryland vacations! Explore topics like:

It may be one of the smallest states, but when it comes to things to do in Maryland, this place is swelling with opportunities. Maryland vacations are packed with culture and fascinating history. The Star Spangled Banner was penned in Baltimore, also home to the FDA and Johns Hopkins, and the United States Naval Academy cozies up to the Chesapeake Bay in Annapolis, the city who hosted the internationally important Middle East Summit.

Maryland is an exciting place to visit, filled with fun, style, and quiet evenings on the shore. In Maryland things to do abound, but visits to Baltimore and Annapolis are sure to keep you busy. See for yourself.


Rated the third best place to shop in the U.S. by Forbe,s and known as a "city of neighborhoods" (it has 72 historic districts), Baltimore is a big, beautiful city with lots to do.
  • The Baltimore Basilica is the oldest Catholic Cathedral in the United States. Designed by Benjamin Latrobe, who also did the United States Capital, the Baltimore Basilica recently underwent a $34 million restoration project. You can get a close up look at this beautiful edifice with or without a guided tour.
  • The National Aquarium hosts hundreds of diverse exhibits ranging from the nearby Chesapeake to the exotic Amazon. Families will love the fish, mammals, birds, and amphibians. Watch a performance at the dolphin show and get a thrill from the 4-D Immersion Theater.
  • The Baltimore Museum of Art houses an internationally renowned collection of over 90,000 works of art from masters such as Matisse, van Gogh, Degas, and Manet. The museum is free, and hosts special exhibitions and events year round. The sculpture gardens are a wonderful way to enjoy art and the beautiful weather.
  • The Neighborhoods of Baltimore are fabulous forays into culture and history. Inner Harbor is a gorgeous port-side spot to enjoy restaurants and shopping, Little Italy is home to a bustling restaurant scene and hosts free outdoor movies, and Fells Point is a beautiful waterfront community you may recognize from the film Sleepless in Seattle.


Located about 30 miles from Washington, D.C, Annapolis is the striking capital city housing a bevy of fabulous things to do in Maryland.
  • The US Naval Academy is a prestigious Navy undergraduate college and a great way to experience the thrills of a day in the life as a Naval Academy student. Tours and interactive exhibits provide a fascinating peek into Navy history, and the thrilling Midshipman formation on the school's gorgeous grounds is quite a display.
  • The Three Centuries Walking Tour is a wonderful way to immerse yourself in the tale of Annapolis. A knowledgeable docent will lead you on a fascinating walk that showcases Annapolis' colonial history, renowned architecture, and significant African Americans.
  • A Pirates of the Chesapeake Cruise is a theatrical adventure that will thrill the young and old. It all starts with the commandeering of a tour boat and takes off, literally, from there. The cruise is perfect for families with pirates of all ages.
  • The Kunta Kinte-Alex Haley Memorial is a beautiful and sobering work sharing the history of the arrival of enslaved Africans to America. Author Alex Haley told the story of his ancestor Kunta Kinte in his Pulitzer Prize-winning book Roots, and this dockside memorial is the spot where Kunte Kinte arrived bound in chains from Africa, visited by over one-million people every year.

Fun in the Great Outdoors

Maryland vacations are home to a lot of natural beauty. From boating on Chesapeake Bay to hanging out on the Ocean City Boardwalk to fishing off a private dock in Deep Creek Lake, the water is never too far away. As a bonus, Maryland's beach and lake towns offer up loads of historical sites and family-friendly attractions that keep people visiting year-round. 

There's a wealth of things to do in Maryland, hidden along its historic streets, beautiful shores, and sparkling cityscapes. What grand things will you do in lovely, diminutive Maryland?

Maryland Vacation Rentals

Largest Fully Refurbished Rental Home in the Historic District

Our home has 14 rooms with seven bedrooms. There are nine (9) working fireplaces, a rear patio with shade garden, a lovely second floor deck overlooking the State House dome, and we are directly across from the beautiful and historic St. John’s Co...

AWESOME BAYVIEWS! Direct Bayfront Topfloor Condo Sleep6

Minimum Age to rent this home is 25 years old. Oceanfront a block away, beautiful clean Bayfront condo with all you can ask for a Vacation Home............The booking Calendar Schedule and Rates posted below are in Real Time. To Reserve your dat...

New Bay Front Condo with Pool Just a Short Walk to the Beach!

Welcome to the Makai, Ocean City Maryland’s newest condominium complex, located on the Isle of Wight Bay on 42nd street, w/ an indoor tropical pool! Enjoy a luxurious open floor plan in this newly built 2 bedroom, 2 full bath, Ocean City condo wi...

Oceanfront and Boardwalk Luxury Condominium

You'll love vacationing in this three bedroom, three bath oceanfront luxury condominium. Relax on the balcony with the beautiful view and the sound of ocean waves. Access balcony from family room and master bedroom suite. The condo has all the ...

Renovated Historic Home Located Downtown -Walk Everywhere!

We welcome you to our fabulous row house on Charles St! You will be delighted by this one of a kind home located right in the heart of the Annapolis Historic District. Built in 1845 and renovated thoughout in 2008 this home retains its original ch...

Vacation Home Search

Find the perfect rental for your vacation

Join Our Newsletter

Get the latest updates in your email