7

Chestertown, MD Houses for Rent

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  • /15

    $2,500 per month

    • 4 Beds
    • 2.5 Baths
    • 2,056 Sq Ft
    • House for Rent

    112 Flying Cloud Dr, Chestertown, MD 21620

    Property Id: 2458980Built in 2023, this beautifully designed 4-bedroom, 2.5-bath home offers 2,056 square feet of modern living in a well-maintained, desirable neighborhood. Thoughtfully laid out with both comfort and functionality in mind, the home features open-concept living spaces, generous natural light, and well-proportioned bedrooms ideal for everyday living or working from

    112 Flying Cloud Dr, Chestertown, MD 21620
  • /26

    $1,520 per month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • House for Rent

    104 Maple Ave Unit 3, 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

    Nick Dively Real Broker, LLC - Annapolis

    104 Maple Ave Unit 3, Chestertown, MD 21620
  • /9

    $1,800 per month

    • 3 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • House for Rent

    8781 Rock Hall Rd, Chestertown, MD 21620

    Property Id: 2461572This is a beautiful & thoughtful 3 bedroom 2 full bath home with a private back yard with a large fire pit great for cook outs and having fun with friends & family. Large front deck adds to the living space that you will love. New heat & air conditioning, upgraded bathrooms and open floor space. $1,800 per month negotiable. If your interested, call or text Chris with

    8781 Rock Hall Rd, Chestertown, MD 21620
  • /5

    $1,000 per month

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

    128 N Queen St Unit 3, Chestertown, MD 21620

    Welcome to 128 N Queen Street, Unit 1. A beautiful Victorian apartment located downtown Chestertown within walking distance to the Chester River and situated close to the Washington College. First floor studio apartment. Unit is available immediately, utilities included: electric, water and sewer. Security Deposit plus one month rent (plus any proration) due at signing. Applications submitted via

    Amanda Morgan Brenton Realty Group

    128 N Queen St Unit 3, Chestertown, MD 21620
  • /33

    $2,800 per month

    • 3 Beds
    • 2 Baths
    • 2,910 Sq Ft
    • House for Rent

    8355 Broad Neck Rd, Chestertown, MD 21620

    Historic charm with modern conveniences, this 3 bedroom home is just minutes from Chestertown. The 6+ acre property is surrounded by woods and farm land offering a lovely, peaceful setting. Grounds maintenance is included in the rent, so just relax and enjoy the beautiful country setting. The old Alms House is located adjacent to the home, but will be used for owner storage and not be available

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    8355 Broad Neck Rd, Chestertown, MD 21620
  • /10

    $3,000 per month

    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • House for Rent

    111 Riverview Place, Chestertown, MD 21620

    Stunning 2 bedroom waterfront guest house just a short walk from Chestertown's historic district. Top to bottom exceptional interior design and brand new finishes from Stoltzfus Brothers Construction. Enjoy summer sunsets of the Chester River and Chestertown's timeless waterfront or take advantage of the dock and private water access. This guesthouse truly celebrates the water views from any

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    111 Riverview Place, Chestertown, MD 21620
  • /27

    $2,050 per month

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • House for Rent

    104 Maple Ave Unit 6, 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

    Nick Dively Real Broker, LLC - Annapolis

    104 Maple Ave Unit 6, Chestertown, MD 21620

Rental Home Trends in Chestertown, MD

Rental Home Trends

Number of Houses for Rent
7
Median Single Family Home Rent
$1,875
Median 3 Bedroom Single Family Home Rent
$2,500
Median 4 Bedroom Single Family Home Rent
$2,225
How to Rent a Home