Chestertown, MD Apartments For Rent
8,654 rentals
Use arrow keys to navigatePET FRIENDLY
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLYTotal price$2,070 - $4,710/mo
Studio-3 Beds
0-2 BathsBeach Street Landing | 700 N Delaware Ave,
Philadelphia, PA 19123
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Use arrow keys to navigateNEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLY$1,685 - $3,335/moStudio-2 Beds1-2 BathsDwell 2nd Street | 1321 N American St,
Philadelphia, PA 19122
Use arrow keys to navigate$2,668 - $5,534/moStudio-2 Beds1-2 BathsAKA University City | 2929 Walnut St,
Philadelphia, PA 19104
Use arrow keys to navigatePET FRIENDLY$1,785 - $3,945/moStudio-2 Beds1-2 BathsThe Keystone Apartments | 417 Callowhill St,
Philadelphia, PA 19123
SPECIAL OFFERPET FRIENDLY
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PET FRIENDLYFURNISHED$2,250 - $2,295/mo1 Bed1 BathThe Terrace on 18th St | 1776 Benjamin Franklin Pkwy,
Philadelphia, PA 19103
SPECIAL OFFERPET FRIENDLY
PET FRIENDLYTotal price$1,499 - $3,600/mo1-3 Beds1-3 BathsThe Tower at Henry | 3232 Henry Ave,
Philadelphia, PA 19129
SPECIAL OFFERPET FRIENDLY$2,510 - $10,171/moStudio-3 Beds1-3 BathsThe Residences at The Bellevue | 200 S Broad St,
Philadelphia, PA 19102
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SPECIAL OFFERPET FRIENDLY$1,454 - $2,315/mo1 Bed1 BathThe Howell - 2101 Washington Ave | 2101 Washington Ave,
Philadelphia, PA 19146
PET FRIENDLY
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SPECIAL OFFERPET FRIENDLYTotal price$1,796 - $3,006/mo1-2 Beds1-2 BathsVia Callowhill | 1201 Callowhill St,
Philadelphia, PA 19123
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SPECIAL OFFERPET FRIENDLYExplore by rental type - Single Family
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Explore by rental type - Townhome
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SPECIAL OFFERPET FRIENDLY$2,125 - $3,850/moStudio-2 bd1-2 baThe Franklin Residences | 834 Chestnut St,
Philadelphia, PA 19107
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SPECIAL OFFERPET FRIENDLY$1,375 - $1,695/mo1-2 bd1 baThe Netherlands Apartments | 4300-4322 Chestnut St,
Philadelphia, PA 19104
Explore by feature - Garage
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NEW - 15 HRS AGOPET FRIENDLY$1,650 - $3,150/moStudio-2 bd1-2 baThe Luxe in Fishtown West | 1705 N American St,
Philadelphia, PA 19122
SPECIAL OFFERPET FRIENDLY
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Explore by rental type - Condo
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- SPECIAL OFFERPET FRIENDLY$2,125 - $3,850/moStudio-2 bd1-2 baThe Franklin Residences | 834 Chestnut St,
Philadelphia, PA 19107 - SPECIAL OFFERPET FRIENDLY
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLY
Explore by feature - Pet Friendly
- SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
- PET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
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- PET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLY$1,375 - $1,695/mo1-2 bd1 baThe Netherlands Apartments | 4300-4322 Chestnut St,
Philadelphia, PA 19104
Explore by feature - Garage
- SPECIAL OFFERPET FRIENDLY
- PET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYFURNISHED
- SPECIAL OFFERPET FRIENDLY
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLY
- NEW - 15 HRS AGOPET FRIENDLY$1,650 - $3,150/moStudio-2 bd1-2 baThe Luxe in Fishtown West | 1705 N American St,
Philadelphia, PA 19122 - SPECIAL OFFERPET FRIENDLY
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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 decreased in Aug 2026 compared to the previous month. Rent previously peaked in Sep 2025.
| Month | Average 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 |
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 bed | 2 beds | 3 beds | 4 beds | All | |
|---|---|---|---|---|---|
| All home types | $1,319 | $1,820 | $1,850 | — | $1,820 |
| Apartments and Condos | $1,319 | $1,820 | — | — | $1,400 |
| Houses | — | $2,400 | $1,783 | — | $1,900 |
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?
- 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.
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