Chestertown, MD Homes for Rent

Property Id: 2282226Welcome to this spacious 2-bedroom, 1-bath apartment located on the second floor of a classic Chestertown multi-family home. This well-laid-out unit offers comfortable living with attractive architectural details and plenty of natural light throughout. Residents also have access to a shared deck, fenced yard, and welcoming front porch, all just minutes from downtown

Property Id: 2282224Welcome to your cozy studio apartment in the heart of Chestertown! This inviting unit blends historic character with modern convenience. The spacious layout highlights original details alongside updated amenities, including an in-unit washer and dryer and central air. Enjoy a fenced yard, a brand-new shared back deck, and a classic front porch—perfect for outdoor

Property Id: 2282225Welcome to your inviting 1-bedroom, 1-bath apartment in the heart of Chestertown. Located in a classic multi-family home on High Street, this residence offers a comfortable layout with attractive architectural details throughout. Outdoor features include a shared deck, a fenced yard, and a welcoming front porch. This well-located rental is available for $1,400 per

Property Id: 1401647This water view apartment has 2 bedroom 1 bath with HVAC on the 2nd floor. Walking distance to downtown restaurants, groceries and shopping. If interested, call or text Chris @ Kendall Properties LLC at for a showing. Credit score must be at least 600 and background check fairly clean.

This is a perfect little house in the country on a 1 acre secluded lot 1 1/2 miles from Chestertown. It is brand new on the inside with high end finishes. New Anderson windows, new doors, tile and laminate floors, SS appliances, granite countertops, Rinnai hot water heater, mini split heat pump, Owner will cut grass and maintain exterior ( 2 tomato plants) for one year, high speed internet

Property Id: 1589400Available for rent: 129A Manor Ave, Chestertown, MD. This charming 3-bedroom, 2-bath home is move-in ready with a brand new HVAC system for year-round comfort. The spacious interior offers a welcoming living space, while the detached 1-bay garage provides the perfect spot for storage or a workshop. Located in a convenient area, this home is ideal for anyone seeking