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Chestertown, MD Homes for Rent

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  • /23

    $1,300 - $1,900 per month

    Kent Crossing Apartments

    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.

    101 Morgnec Rd, Chestertown, MD 21620
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    $1,300 per month

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

    101 Morgnec Rd, Chestertown, MD 21620

    One, two and three bedroom apartments located near Washington College, wellness/ rehab center, Churches, shopping and a short walk to downtown Chestertown. Short distance to the Chester River and Chesapeake Bay. Immediate Availability.

    Herschell Claggett Davis Real Estate, Inc.

    101 Morgnec Rd, Chestertown, MD 21620
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    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft
    • House for Rent

    129a Manor Ave N, Chestertown, MD 21620

    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

    129a Manor Ave N, Chestertown, MD 21620
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    $1,400 per month

    • 2 Beds
    • 1 Bath
    • House for Rent

    118 N Water St, Chestertown, MD 21620

    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.

    118 N Water St, Chestertown, MD 21620
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    $2,000 per month

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

    7121 Quaker Neck Rd, Chestertown, MD 21620

    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

    7121 Quaker Neck Rd, 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

What are the most popular neighborhoods in Chestertown, MD for renters?
The most popular neighborhood in Chestertown, MD for renters is Hollywoods.
What are the most popular zip codes in Chestertown, MD for renters?
The most popular zip codes in Chestertown, MD for renters include 21620, 21220, 21040, 21001 and 21009.
How to Rent a Home