Annapolis Vacation Rentals

Your Vacation Destination Starts Here

Specializing in Annapolis Rentals including Corporate Housing, Commissioning Week, Boat Shows and more! 

Located on Chesapeake Bay, Annapolis, MD is a city steeped in history. The city was home to its own Annapolis Tea Party in 1774. The burning of the ship Peggy Stewart who arrived from London filled with tea and its dreaded taxation without representation ended tea import during colonial rule with England. Now, historic Annapolis is a vacation destination for history buffs and sailing aficionados alike. Book an Annapolis vacation rental today to experience the charm of this sailing port city! 

Annapolis Attractions: 

Annapolis is not lacking in historic attractions. Three signers of the Declaration of Independence called Annapolis home and you may visit their expansive homes and formal gardens through daily or weekly tours. Check out the historic homes and even more attractions during your Annapolis vacation!  

• US Naval Academy 
• St. John’s College 
• Schooner Woodwind Annapolis Sailing Cruises
• Annapolis Yacht Club 
• The Maryland State House 

Annapolis Events: 

On top of offering plenty of historical sites and attractions, Annapolis is also host to a variety of events. USNA Friends and Family – We offer homes for the whole family located within walking distance to the Academy and the USNA Stadium. Plan ahead and for those special visits: Commissioning Week, parent’s weekend and sporting events. Contact our office for more information and sign up for “Spot your Plebe.” Check out some of the highlighted events that can be experienced in Annapolis:  

• United States Sailboat Show 
• United States Powerboat Show 
• United States Naval Academy Commissioning Week
• Annapolis Crab Feast
• Annapolis Oyster Fest
• Annapolis Art Week

Annapolis Vacation Rentals

To compliment your visit to historic Annapolis, we offer a unique Annapolis Rentals Program. Our short-term weekend, weekly or monthly program packages supplement the major hotel chains already in Annapolis. Annapolis vacation rentals heighten the uniqueness of a visit to our historic sailing city by offering you a stay in individually owned homes, townhouses and condo’s. Come for a weekend and enjoy a sail on the Schooner Woodwind, enjoy the Harbor Queen or take a water taxi from your restaurant to other local destinations. Picture your romantic weekend getaway enjoying the ambiance of living in an historic home. All of our rental homes are owned by Annapolis residents who treasure our pleasant living on the Chesapeake Bay. Pride of ownership in an historic Annapolis home will provide distinctive memories linked to our city’s historic significance in America’s growth as a nation. 

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About Long & Foster:

"Service is remembered long after price is forgotten!"

Long & Foster, Annapolis Rentals will provide our guests and hosts with a pleasant rental experience through one convenient, professional and community-oriented office. We are passionate about making family vacations, rich, memorable, and worry-free. Annapolis is your destination city whether you are a sailor, government official, United States Naval Academy or St. John’s College affiliate, or simply a history buff. Annapolis is a charming, historic destination for a day, a weekend or a month(s). Our goal is to facilitate a wholesome and heart-warming stay in Annapolis.

By offering full services (rental, reservations, and cleaning services) our customer oriented staff will take the hassle out of your planning. Check out our community calendar of events when planning your stay in Annapolis so you can take advantage of everything Annapolis has to offer. Contact us to schedule your lodging in Annapolis, Maryland today!