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Chestertown Homes for Rent

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  • /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
  • /38

    $2,175 per month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    104 Maple Ave, Chestertown, MD 21620

    Welcome to your new home in the heart of Chestertown Maryland, a charming historic town nestled along the Chester River, known for its vibrant arts scene, waterfront dining, and small-town charm.This beautifully designed property blends modern finishes with timeless appeal. Step inside to find engineered hardwood floors flowing throughout the main living areas, creating both warmth and

    Nicolas Dively Real Broker, LLC - Annapolis

    104 Maple Ave, Chestertown, MD 21620
  • /20

    $1,300 per month

    • 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 persons. No pets or smoking.

    200 Cannon St Unit 1A, 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
  • /2

    $2,100 per month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    866 Washington Ave, Chestertown, MD 21620

    Just about everything you need is within five minutes of home. You will save time to enjoy parks and entertainment that are continuously held in Chestertown..

    866 Washington Ave, 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
  • /19

    $2,500 per month

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

    202 High St Unit A, Chestertown, MD 21620

    Property Id: 2081475Spacious 2 bedroom apartment in downtown Chestertown with a front row seat to the Tea Party. Open kitchen/living/dining room, with stainless appliances, dishwasher and granite counters. Two large bedrooms on opposite ends of the apartment. In-unit washer and dryer. The building has recently undergone extensive renovations, with secure access and many energy

    202 High St Unit A, Chestertown, MD 21620

Frequently Asked Questions Why Live in Chestertown

What are the most popular neighborhoods for renters near Chestertown?
The most popular neighborhoods for renters near Chestertown are Hollywoods and Constant Friendship.
What are the most popular zip codes for renters near Chestertown?
The most popular zip codes for renters near Chestertown are 21620, 21219, 21220, 21221 and 21085.
How to Rent a Home