Chestertown, MD Apartments For Rent

25 rentals

Apartments For Rent Near Chestertown, MD

We found 7 more apartments matching your filters just outside Chestertown

What Locals Say about Chestertown

  • Trulia User
    "Washington park is a great, safe and family oriented are!! I’ve never live there permanently but by mom is from that are and my grandparents still live there!! I live always visiting! And hope to have a hoke there myself one day!!!"
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  • Trulia User
    "Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
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  • Trulia User
    "I lived in this neighborhood for tens you’d and the community is very friendly. Community clean up after their dog and they watch over one another "
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  • Kesha C.
    "Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
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  • Tracy W.
    "The schools are better in Queen Anne's County. The town is well-maintained, and houses and businesses in town have to meet the strict guidelines of the historical society. Restaurants are generally mediocre in quality and high in price. "
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  • Rancraw
    "This is just a great place to live. I am from Dallas, TX, I have lived in six countries, DC, and Miami. This is my favorite place to live. ONLY down side is getting to an airport under an hour."
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  • Acaldwell1297
    "I am basically on the main road.... pretty easy to get in and out. I don’t live far from work! So pretty easy for me "
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  • Guillermo A.
    "Good Community, friendly people, good services. "
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  • Nancy M.
    "People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
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  • asso
    "Quiet - not for night owls. Nice farmer's market, good library. Easy acess for weekends in DC, Baltimore, Philly, & Ocean Beaches. College town, Chester River"
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  • Dafoster
    "Historic town along the Chester River and home to Washington College. Convenient to shops, restaurants, farmers market, waterfront, Garfield Center for the Arts and College Activities. A walker's paradise and a favorite for bikers and boaters."
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Average Rent Trends in Chestertown, MD

Rent in Chestertown, MD varies by number of bedrooms and home type. Use these charts to quickly see how rent changes.
Average rent decreased in Aug 2026 compared to the previous month. Rent previously peaked in Sep 2025.
MonthAverage rent
Sep 2025$2,400
Oct 2025$2,100
Nov 2025$2,100
Dec 2025$2,000
Jan 2026$1,575
Feb 2026$1,900
Mar 2026$2,000
Apr 2026$2,000
May 2026$1,520
Jun 2026$2,050
Jul 2026$2,000
Aug 2026$1,920
View as a graph

Average Rent By Bedroom and Home Type

In August 2026, Apartments and Condos were the most affordable home type to rent compared with Houses.
1 bed2 beds3 beds4 bedsAll
All home types$1,319$1,820$1,850—$1,820
Apartments and Condos$1,319$1,820——$1,350
Houses—$2,400$1,900—$1,900
See more information about local market trends in Chestertown, MD

Frequently Asked Questions about Rentals in Chestertown, MD

  • What is the average rent of an apartment in Chestertown, MD?
    The average rent of an apartment in Chestertown, MD is $1,319 per month. This is about 33% lower than the national average.
  • When is the average rent cheapest in Chestertown, MD?
    In the last year, the average rent in Chestertown, MD was lowest in Jan 2025 when it was $1,400 per month.
  • When is the average rent most expensive in Chestertown, MD?
    In the last year, the average rent in Chestertown, MD was highest in Sep 2025 when it was $2,400 per month.
  • How does the rent of a 1 bedroom apartment compare to a studio apartment in Chestertown, MD?
    The average rent of a 1 bedroom apartment in Chestertown, MD is $1,319 per month. That is about $344 more than the cost of a studio apartment.
  • How many available rental listings are in Chestertown, MD?
    There are 7 available rental listings in Chestertown, MD.
  • What are some zip codes in Chestertown, MD?
    Chestertown, MD includes zip codes such as: 21620, 21690.
  • What are some cities near Chestertown, MD?
    Some nearby cities include: Worton, Still Pond, Rock Hall, Church Hill, Kennedyville. These cities may have more rental options to explore.
View this page in Spanish: Chestertown, MD Apartments For Rent - 65 Rentals | Trulia