Apartments for Rent in Chestertown, MD

This inviting 1-bedroom, 1-bath apartment features attractive architectural details and a comfortable layout. Enjoy a shared deck, fenced yard, and a welcoming front porch. Located in a classic multi-family home, it offers pet-friendly living with easy access to local amenities. The apartment is available for $1,400/month starting February 2026, providing a cozy retreat in Chestertown. Additional features include in-unit laundry and beautiful hardwood floors.

This spacious 2-bedroom, 1-bath apartment on the second floor boasts attractive architectural details and abundant natural light. Enjoy a shared deck, fenced yard, and welcoming front porch, all within minutes of downtown shops and parks. A perfect blend of comfort and convenience, ideal for pet lovers. Rent includes common area maintenance; utilities are tenants' responsibility. Available for $1,575 starting February 2026.

This inviting studio apartment seamlessly blends historic character and modern convenience. With original details and updated amenities, it features an in-unit washer/dryer, central air, and a brand-new shared back deck. Enjoy outdoor living in a fenced yard or relax on the classic front porch. Ideal for pet lovers, this cozy space offers a unique rental experience in Chestertown, all for $900 per month.

This welcoming 3-bedroom, 2-bath home features fresh paint and a brand-new HVAC system, ensuring year-round comfort. The spacious interior is perfect for comfortable living, while the detached 1-bay garage offers ample storage or workshop space. Ideally situated for convenience, this home encompasses comfort and functionality for a delightful living experience.

Enjoy stunning water views in this pet-friendly 2-bedroom, 1-bath apartment, ideally located just a stroll away from downtown’s shops and eateries. This second-floor unit features hardwood floors, HVAC, and in-unit laundry for convenience. Perfect for those seeking a blend of comfort and vibrant community living!