5

Chestertown, MD Homes for Rent

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  • /23

    Starting at $1,300 Per Month

    • 1 - 3 Beds

    101 Morgnec Rd, Chestertown, MD 21620

    Quiet community, beautifully landscaped. Close to Washington College, can walk to downtown historic Chestertown and shops. A must see.

    Kent Crossing Apartments

    101 Morgnec Rd, Chestertown, MD 21620
  • /20

    $1,300

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 580 Sq Ft
    • Condo for Rent

    200 Cannon St Unit 1A, Chestertown, MD 21620

    Ground floor apartment in nice, safe, quiet, upscale area 2 blocks from river and waterfront park, 1 block from downtown (in Historic District). Suitable for 1 person. No pets or smoking.

    200 Cannon St Unit 1A, Chestertown, MD 21620
  • /10

    $1,450 Per Month

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    128 N Queen St Unit 3, Chestertown, MD 21620

    Welcome to 128 N Queen Street, Unit 2. Utilities included!!!A beautiful Victorian apartment located downtown Chestertown within walking distance to the Chester River and situated close to the Washington College. 2nd floor private unit with spacious living area, separate dining room, galley kitchen, full bathroom and bedroom. All with a fresh coat of paint! Unit is available immediately,

    Amanda Morgan Brenton Realty Group

    128 N Queen St Unit 3, Chestertown, MD 21620
  • /7

    $1,495 Per Month

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    104 Maple Ave Unit 3, Chestertown, MD 21620

    Nick Dively Real Broker, LLC - Annapolis

    104 Maple Ave Unit 3, Chestertown, MD 21620
  • /17

    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    7501 Church Hill Rd Unit 5, Chestertown, MD 21620

    If you’ve been searching for an open‑concept apartment with a stunning view, your search ends here. This fully renovated third‑floor residence delivers modern style, thoughtful updates, and an airy layout that feels instantly welcoming.Step into a beautifully redesigned kitchen featuring ample cabinetry, upgraded appliances, and a spacious island perfect for cooking, gathering, or

    Amanda Morgan Brenton Realty Group

    7501 Church Hill Rd Unit 5, Chestertown, MD 21620

Why Live in Chestertown

Chestertown, Maryland, is a historic community on the Chester River, known for its maritime heritage and charming downtown. Founded in 1706, Chestertown was once a bustling port and remains a popular destination for homebuyers seeking a quieter lifestyle away from larger cities like Washington or Philadelphia. The town features a mix of Victorian homes downtown and waterfront properties, with river access being a significant draw. Residents enjoy boating on the river, and many homes feature private docks. The private Chester River Yacht & Country Club offers additional amenities such as an 18-hole golf course and a marina. Local parks like Wilmer Park provide walking trails and playgrounds, while the Wayne Gilchrest Trail caters to bikers and joggers. Downtown Chestertown is pedestrian-friendly, hosting boutiques, galleries and locally owned restaurants. Annual events like the Chestertown Tea Party Festival and the Sultana Downrigging Festival celebrate the town's rich history. Washington College, a small liberal arts institution, adds to the vibrant atmosphere. The University of Maryland Shore Medical Center provides health care services, including an emergency room. Chestertown is within driving distance of Baltimore, 75 miles away, and Baltimore/Washington International Airport. With its blend of historic charm, riverfront recreation and local amenities, Chestertown offers a unique living experience.

Frequently Asked Questions

How much does it cost to rent a home in Chestertown, MD?
The median rent for a home in Chestertown, MD is $1,472 per month, though prices vary by neighborhood, size, and property type. As of September 2026, condos tend to be the most affordable option while single-family homes and townhouses are currently more expensive.
How much do you need to make to afford rent in Chestertown, MD?
To comfortably afford the median rent in Chestertown, MD, a household needs to earn roughly $58,880 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $1,472 per month in Chestertown, MD, renters typically need to show $4,416 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Chestertown, MD?
In Chestertown, MD, the price-to-rent ratio is 21.1, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.

Rental Home Trends

Number of Homes for Rent
5
Median Rent
$1,472
Median Single Family Home Rent
$1,658
Median Townhouse Rent
$2,000
Median Condo Rent
$1,550
How to Rent a Home