6

Chestertown, MD Homes for Rent

Section Image
  • 101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    /23

    $1,300 - $2,000 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
  • 114 Conley Dr, Chestertown, MD 21620
    114 Conley Dr, Chestertown, MD 21620
    114 Conley Dr, Chestertown, MD 21620
    /19

    $1,700 per month

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft
    • Townhouse for Rent

    114 Conley Dr, Chestertown, MD 21620

    Immaculate 3 bedroom, 1.5 bathroom townhouse available for rent! Rent includes water/sewer and lawn care. All you have to do is move in! Apply using online rent spree link. To qualify applicants must have 580+ credit and gross income near 3X rent. No pets permitted. Tenant occupied until the end of July and will be available for occupancy by mid August.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    114 Conley Dr, Chestertown, MD 21620
  • 5117 Deep Point Dr, Chestertown, MD 21620
    5117 Deep Point Dr, Chestertown, MD 21620
    5117 Deep Point Dr, Chestertown, MD 21620
    /25

    $3,200 per month

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    5117 Deep Point Dr, Chestertown, MD 21620

    Welcome home to historic Overbeck! This beautiful old home overlooks an expansive yard and on to the Chester River. The small beach is a perfect launch site for your paddle boards and kayaks. Inside find fireplaces, hardwood floors on main level along with brick floored sunroom. Great big fireplace in Kitchen then up a few stairs to formal dining room . Cozy living room with covered porch on

    Julie Cary Rosendale Realty

    5117 Deep Point Dr, Chestertown, MD 21620
  • 128 N Queen St Unit 4, Chestertown, MD 21620
    128 N Queen St Unit 4, Chestertown, MD 21620
    128 N Queen St Unit 4, Chestertown, MD 21620
    /10

    $1,450 per month

    • 1 Bed
    • 1 Bath
    • 1,455 Sq Ft
    • Condo for Rent

    128 N Queen St Unit 4, Chestertown, MD 21620

    Move in ready 2nd floor apartment in Downtown Chestertown. One spacious bedroom, full bathroom, living area and a step-up cove/office space. Conveniently located within walking distance to the Chester River. Utilities included with the exception of Internet/Cable. All applicants apply through Rent Spree.

    Amanda Morgan Brenton Realty Group

    128 N Queen St Unit 4, Chestertown, MD 21620
  • 7401 Church Hill Rd Unit 5, Chestertown, MD 21620
    7401 Church Hill Rd Unit 5, Chestertown, MD 21620
    7401 Church Hill Rd Unit 5, Chestertown, MD 21620
    /13

    $2,100 per month

    • 2 Beds
    • 1 Bath
    • 1,344 Sq Ft
    • Condo for Rent

    7401 Church Hill Rd Unit 5, Chestertown, MD 21620

    Lovely 2 Bedroom, 1 Bathroom rental available June 1st! This spacious floorplan on the top floor has beautiful views of the Chester River. Open Kitchen/Dining/Living area that opens to the water view balcony. Newly remodeled Kitchen and bathroom. Applications accepted via rentspree. Don't wait, this one will be gone quick!

    Amanda Morgan Brenton Realty Group

    7401 Church Hill Rd Unit 5, Chestertown, MD 21620
  • 101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    /11

    $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
Maryland Chestertown

Homes for Rent in Chestertown, MD

Frequently Asked Questions

What are the most popular neighborhoods in Chestertown, MD for renters?
The most popular neighborhoods in Chestertown, MD for renters are Bowleys Quarters, Joppa and Constant Friendship.
What are the most popular zip codes in Chestertown, MD for renters?
The most popular zip codes in Chestertown, MD for renters include 21009, 21040, 21015, 21220 and 21619.
How to Rent a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group