Chestertown Apartments and Rentals
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View detailed rental listings for Chestertown apartments, condos, townhomes, and houses for rent— including photos, floor plans, and virtual tours.
Featured Apartments in Chestertown, MD
Kent Crossing Apartments
Close to shopping center and downtown Chestertown...Near hospital and Washington College and Chester River...Historic Chestertown and Easy access and Rt 213 and Rt 301...
Chestertown MD, 21620
Colonial Manor Apartments
Convenient to shopping center, restaurants and schools...Near hospital, Washington College and Chester River...Located in Historic Chestertown and easy access to Rt 213 and Rt 301
Chestertown MD, 21620
Charlesmont
Close to Schools...Minutes from I-695 & I-95...Close to Shopping Centers...
Chestertown MD, 21222
Mansfield Woods II
Convenient location, close to shopping, schools and major access routes...Private intercom entry at the main door...24-hour emergency maintenance....
Chestertown MD, 21221
Mansfield Woods
Convenient location, close to shopping, schools and major access routes...Private intercom entry at the main door...24-hour emergency maintenance....
Chestertown MD, 21221

Chestertown, MD
Overview of Chestertown
Tucked away in the banks of the Chester River, the city of Chestertown, Md., is a great location for growing families to live, work and play. The heritage of the Chesapeake Bay is alive and well in this charming small town, attracting many Maryland residents to make Chestertown apartments for rent their new home. Full of recreational activity and seaside fare that has made the tri-state area famous, Chestertown is continually growing and thriving. According to City-Data, Chestertown saw a 10 percent increase in population from 2000 to 2010, making it a heavily sought-after community in the Chesapeake Bay area. There is nothing quite as charming as living in Maryland's upper eastern shoreline, so the city is certainly showing no signs of slowing down.
Living in Chestertown, MD
Chestertown has been part of the Mid-Atlantic since 1706, but the real excitement around this city is just now starting to take shape. According to City-Data, is extremely affordable compared to other communities surrounding Baltimore and Philadelphia. With a cost of living index that is more than 10 percent below the U.S. average, it makes sense that so many people are beginning to call Chestertown home. According to information from the 2010 U.S. Census Bureau, there are more than 5,000 residents living in the city, and that number is expected to grow as more people find out about what this quaint small town has to offer.
Chestertown Attractions and Special Events
One of the biggest community events held every Memorial Day Weekend in Chestertown is the annual Tea Party Festival. Legend has it that on the eve of the famous Boston Tea Party in 1774, Chestertown shut down their ports in solidarity with the patriots in Massachusetts, and the citizens in the area have been celebrating this occasion on Maryland's eastern shore for many years. Included among the festivities are a cocktail party, colonial parade, tea toss, colonial crafts and live musical entertainment.
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