USA & Canada: (877)-290-4447 | En Mexico: (800) 894 - 5636
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USA & Canada: (877)-290-4447 | En Mexico: (800) 894 - 5636
Randell Smith loves the historic homes and waterfront views, as well as the ongoing building and growth in Annapolis, MD. With over two decades of leadership experience across numerous fields, he brings a strategic and engaging approach to vacation rental and portfolio management.
Randell’s background encompasses honorable service in the U.S. Army Medical Service Corps, followed by earning his Juris Doctorate in 2013. His leadership experience spans from legal and financial services to insurance defense and entrepreneurship. Having entered the vacation rental industry through real estate investments, he has managed a growing portfolio of long and short-term rentals for several years.
Beyond business, he’s a husband for over two decades and a father of three, Randell is active in his community and family life. He is an active member of the Anne Arundel County Association of Realtors (AACAR), Vacation Rental Management Association (VRMA), National Association of Property Managers (NARPM), National Association of Realtors (NAR), Member of the Virginia Chamber of Commerce, and Member of the National Notary Association.
Randell values creating exceptional guest experiences, and believes the differential strength of Casago Annapolis lies in combining hospitality, operational efficiency, and a people-first mindset.
Located on the banks of the Severn River and Chesapeake Bay, Maryland’s capital city invites guests to explore its historic architecture, fresh seafood, brick-lined streets, and vibrant waterfront. This year-round coastal destination offers colonial charm paired with nautical adventures for visitors of all ages.
Largely considered part of the Baltimore-Washington Metro Area, Annapolis is just a 45-minute drive to Washington, D.C. or Baltimore. This makes it a terrific spot to cast off for exploring the eastern seaboard, offering over 500 miles of shoreline in Anne Arundel County, along with scenic rivers, creeks, and trails.
Known as the “Sailing Capital of the World,” Annapolis, Maryland is deeply rooted in its historic maritime heritage and is home to the US Naval Academy. Families and groups frequently visit midshipmen at the Naval Academy, while Commissioning Week each May is a time-honored tradition filled with celebration and fanfare.
Along with its seafaring legacy, the academic and historic atmosphere in Annapolis extends to the campus of St. John’s College. History buffs can appreciate the State House in Annapolis as the oldest in continuous legislative use in the nation, or visit the home of William Paca, one of Maryland’s signers of the Declaration of Independence.
With its mix of maritime culture, history, and year-round appeal, Annapolis is a consistently attractive getaway for families and history enthusiasts alike. Plan a visit to discover why this historic seaport remains a favorite treasure of the Chesapeake Bay.
There are three international airports providing easy access to Annapolis: Baltimore-Washington International Thurgood Marshall Airport (BWI), Ronald Reagan Washington National Airport (DCA), and Washington Dulles International Airport (IAD). The BWI Thurgood Marshall Airport is located in Anne Arundel County, Maryland and just about 20 miles from Annapolis.
Annapolis is a year-round coastal destination, but the city truly comes alive from April through October, when mild temperatures and waterfront breezes create perfect conditions for sailing, dining, and exploring its historic streets.
Spring welcomes visitors with cherry blossoms along the shoreline, vibrant boating activity, and the start of festival season.
Summer is peak travel time, drawing families, Mid-Atlantic vacationers, and boating enthusiasts to the Chesapeake Bay for sailing charters, crab feasts, and lively harbor events.
Fall is considered one of the best-kept secrets in Annapolis, offering warm days, crisp evenings, and stunning waterfront foliage—ideal for romantic getaways, maritime experiences, and the energetic atmosphere surrounding the U.S. Naval Academy’s football season.
In winter, the city maintains strong appeal with holiday lights, cozy waterfront restaurants, and historic tours, giving travelers a charming off-season experience.
High: March – September
Low: January-February; October – December
Annapolis is very family-friendly, with several attractions near the City Dock and a high walkability factor throughout the historic downtown and some of the surrounding older neighborhoods. Street parking, metered parking, and parking garages are available in and around downtown, though stay alert to city events (especially at the Naval Academy) that can increase traffic.
Many of the biggest events in Annapolis center around the area’s rich maritime history as well as events at the U.S. Naval Academy:
