Chestertown, MD Apartments For Rent
368 rentals
Use arrow keys to navigateNEW - 19 HRS AGOPET FRIENDLYTotal price$2,662 - $4,499/mo
Studio-2 Beds
1-2 BathsCenter & Stone | 1190 Hancock St #S210,
Quincy, MA 02169
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLYTotal price$3,130 - $3,191/mo2 Beds2 BathsAlister Quincy | 500 Falls Blvd #A-A-1202,
Quincy, MA 02169
Use arrow keys to navigatePET FRIENDLY
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLY
Use arrow keys to navigatePET FRIENDLY
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLYTotal price$2,431 - $3,746/moStudio-2 Beds1-2 BathsAvalon Quincy Adams | 269 Centre St #c2e13b8f2,
Quincy, MA 02169
Use arrow keys to navigateNEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYFURNISHED$2,472 - $3,421/moFees may apply1-2 Beds1-2 BathsHighPoint | 12 Highpoint Cir #8812,
Quincy, MA 02169
PET FRIENDLYFURNISHED$2,195 - $2,600/moFees may applyStudio-2 Beds1 BathFurnished Rentals - Quincy/South Shore | 33 Furnace Ave #18,
Quincy, MA 02169
PET FRIENDLY
PET FRIENDLY$2,704 - $3,897/moFees may apply1-2 Beds1-2 BathsNeponset Landing | 2 Hancock St #1016,
Quincy, MA 02171
SPECIAL OFFERPET FRIENDLY
PET FRIENDLYTotal price$2,250 - $3,000/moStudio-2 Beds1-2 BathsGamma North Quincy | 95 W Squantum St #706,
Quincy, MA 02171
SPECIAL OFFERPET FRIENDLYTotal price$2,609 - $3,546/mo1-2 Beds1-2 BathsWest of Chestnut | 21 Chestnut St #307,
Quincy, MA 02169
PET FRIENDLYTotal price$2,600 - $3,894/moStudio-2 Beds1-2 BathsThe Abby | 255 Hancock St #3444,
Quincy, MA 02171
NEW - 2 DAYS AGOSPECIAL OFFERPET FRIENDLYTotal price$2,080 - $2,835/moStudio-2 Beds1 BathQuincy Commons | 1 Canton Rd #10045,
Quincy, MA 02171
PET FRIENDLYTotal price$2,845 - $4,425/mo1-3 Beds1-2 BathsQuarry Hills | 333 Ricciuti Dr #4-0436,
Quincy, MA 02169
PET FRIENDLY
NEW - 1 DAY AGOPET FRIENDLYTotal price$2,338 - $2,832/mo1-2 Beds1-2 BathsFaxon Commons | 1037 Southern Artery #995408,
Quincy, MA 02169
PET FRIENDLY$3,261 - $4,642/moFees may apply1-2 Beds1-2 BathsWindsor Marina Bay | 552 Victory Rd #S208,
Quincy, MA 02171
SPECIAL OFFERPET FRIENDLYTotal price$2,478 - $3,363/moStudio-2 Beds1-2 BathsAvalon Quincy | 229 Quarry St #1B-1Ba-855Sqft,
Quincy, MA 02169
SPECIAL OFFERPET FRIENDLYTotal price$2,379 - $3,090/moStudio-1 Bed1 BathDeco | 625 Thomas E Burgin Pkwy #345,
Quincy, MA 02169
PET FRIENDLY
SPECIAL OFFERPET FRIENDLY
PET FRIENDLY$2,250 - $2,900/moFees may apply1-2 Beds1 BathPresidential Estates | 1020 Southern Artery #54-5,
Quincy, MA 02169
PET FRIENDLYTotal price$2,348 - $2,862/mo1-2 Beds1-2 Bathseaves Quincy | 150 Quarry St #2B-1Ba-1075Sqft,
Quincy, MA 02169
PET FRIENDLY$2,200 - $3,000/moFees may applyStudio-2 Beds1-2 BathsNova Quincy | 1500 Hancock St #613,
Quincy, MA 02169
PET FRIENDLY
SPECIAL OFFERPET FRIENDLYTotal price$2,350 - $3,060/mo1-2 Beds1-2 BathsLincoln Heights | 175 Centre St #00M-1301,
Quincy, MA 02169
PET FRIENDLY
NEW - 1 DAY AGOPET FRIENDLY$2,575 - $3,200/moFees may apply1-2 Beds1-2 BathsHillside Residence | 23 Bridge St #215,
Quincy, MA 02169
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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 | $1,200 | $1,700 | $2,200 | $2,500 | $2,050 |
| Apartments and Condos | $1,200 | $2,050 | — | — | $1,500 |
| Houses | — | $1,400 | $2,044 | $2,500 | $2,400 |
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 $1,500 per month. This is about 23% 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 $2,400 per month. This is about 23% 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 9 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.