Chestertown, MD Apartments For Rent
367 rentals
- NEW - 1 DAY AGOPET FRIENDLY$1,825 - $2,495/mo1-2 Beds1-2 BathsPARQ at the Square | 1303 Delaware Ave #0201,
Wilmington, DE 19806 - PET FRIENDLY
- PET FRIENDLY$1,405 - $2,217/moStudio-3 Beds1-2 BathsTop of the Hill Apartments | 2101 Prior Rd #919C,
Wilmington, DE 19809 - PET FRIENDLY
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLY
- NEW - 6 HRS AGOPET FRIENDLY$1,795 - $3,495/moStudio-2 Beds1-2 Baths101 Avenue of the Arts | 101 Avenue Of The Arts #302,
Wilmington, DE 19801 - NEW - 1 DAY AGOPET FRIENDLY$1,485 - $2,600/mo1-3 Beds1-3 BathsValley Run | 2601 Carpenter Station Rd #RP-2206RP,
Wilmington, DE 19810 - $1,545 - $1,985/mo1-2 Beds1-2 BathsMarket View Residences | 913 N Market St #1008,
Wilmington, DE 19801 - $1,395 - $1,425/mo1 Bed1 BathThe Square at Trolley | 1303A Delaware Ave #1301-4E,
Wilmington, DE 19806 - $1,292 - $2,122/moStudio-2 Beds1-2 BathsStratford Apartments | 3120 Naamans Rd #G003,
Wilmington, DE 19810 - $1,750 - $2,615/moStudio-2 Beds1-2 BathsLuxor Lifestyle Apartments Wilmington | 340 S Market St #1-108,
Wilmington, DE 19801 - $1,297 - $1,847/mo1-2 Beds1-2 BathsFairway Park Apartments & Townhomes | 5561 Limeric Cir #2142,
Wilmington, DE 19808 - $1,150 - $1,675/mo1-2 Beds1-2 BathsBrandywine Apartments | 2726 Jacqueline Dr #F08,
Wilmington, DE 19810 - $1,275 - $1,575/mo1-2 Beds1-2 BathsThe Reserve at Mill Creek Apartment Homes | 131 Scarborough Park Dr #9760834e8,
Wilmington, DE 19804 - $1,525 - $2,500/mo1-2 Beds1-2 BathsThe Colony Apartments | 2 Colony Blvd #12-44,
Wilmington, DE 19802 - Total price$1,565 - $2,255/mo1-3 Beds1-2 BathsVillage at Fox Point | 1436 Kynlyn Dr #P-1229,
Wilmington, DE 19809 - $1,400 - $1,700/mo1-2 Beds1-2 BathsArundel Apartments | 2901 Crossfork Dr #83e47e345,
Wilmington, DE 19808 - $1,450 - $1,550/mo1-2 Beds1 BathThe Crossings at Limestone Apartments | 4605 Patrician Blvd #4631F,
Wilmington, DE 19808 - $1,640 - $2,605/moStudio-2 Beds1-2 BathsRiver House Apartments | 401 A St #511,
Wilmington, DE 19801 - $1,525 - $1,695/mo2 Beds2 BathsLighthouse Hill Apartments | 1204 Terra Hill Dr #1208-3C,
Wilmington, DE 19809 - $1,360 - $2,250/moStudio-2 Beds1-2 BathsThe Residences at Mid-town Park | 116 W 9th St #856,
Wilmington, DE 19801 - $1,499 - $2,899/mo1-2 Beds1-2 BathsThe Lofts at 2nd and LOMA | 215 N Market St #218,
Wilmington, DE 19801 - $1,430 - $2,205/mo1-2 Beds1-2 BathsThe Residences at Justison Landing | 331 Justison St #J217,
Wilmington, DE 19801 - $1,750 - $2,800/mo1-2 Beds1-2 BathsThe Residences at Harlan Flats | 401 Justison St #349,
Wilmington, DE 19801 - $1,525 - $2,796/mo1-2 Beds1-2 BathsThe Residences at Christina Landing | 115 Christina Landing Dr #902,
Wilmington, DE 19801 - $1,285 - $1,535/mo1-2 Beds1 BathHeritage Court Apartments | 5597-2B Heritage Court Dr #55893B,
Wilmington, DE 19808 - $1,300 - $1,500/mo1-2 Beds1 BathLea Boulevard Apartments | 608 W Lea Blvd #43c2ea2b7,
Wilmington, DE 19802 Explore by rental type - Single Family
Explore by rental type - Townhome
Explore by feature - Air Conditioning
Explore by feature - Pet Friendly
Explore by feature - Garage
Explore by rental type - Single Family
Explore by rental type - Townhome
Explore by feature - Air Conditioning
Explore by feature - Pet Friendly
Explore by feature - Garage
What Locals Say about Chestertown
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 increased in Jun 2026 compared to the previous month. Rent previously peaked in Sep 2025.
| Month | Average rent |
|---|---|
| Jul 2025 | $1,500 |
| Aug 2025 | $1,600 |
| 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 |
Average Rent By Bedroom and Home Type
In June 2026, Apartments and Condos were the most affordable home type to rent compared with Houses.
| 1 bed | 2 beds | 3 beds | 4 beds | All | |
|---|---|---|---|---|---|
| All home types | $1,500 | $1,700 | $2,600 | $2,422 | $2,050 |
| Apartments and Condos | $1,500 | $1,700 | — | — | $1,700 |
| Houses | — | — | $2,200 | $2,422 | $2,600 |
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 $1,700 per month. This is about 13% lower than the national average.
- What is the average rent of a house in Chestertown, MD?The average rent of a house in Chestertown, MD is $2,600 per month. This is about 33% higher 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 many available rental listings are in Chestertown, MD?There are 5 available rental listings in Chestertown, MD.
- What are some zip codes in Chestertown, MD?
- 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.