Chestertown, MD Apartments For Rent
214 rentals
Use arrow keys to navigateNEW - 1 DAY AGOPET FRIENDLYTotal price$1,597 - $2,038/mo
1-3 Beds
1-2 BathsParkside Apartments | 2831 SE Palmquist Rd,
Gresham, OR 97080
Use arrow keys to navigateNEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYTotal price$1,591 - $2,294/mo1-3 Beds1-2 BathsAvana Powell Valley | 1500 SW Pleasant View Dr,
Gresham, OR 97080
Use arrow keys to navigatePET FRIENDLY
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLY$1,225 - $1,925/moStudio-2 Beds1 BathWoodland Flats Apartments | 2752 NE Hogan Dr,
Gresham, OR 97030
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLY
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLY
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLYTotal price$1,499 - $2,250/mo1-3 Beds1-2 BathsTwelve Mile Crossing | 588 SE 217th Ave,
Gresham, OR 97030
NEW - 1 DAY AGOPET FRIENDLY
SPECIAL OFFERPET FRIENDLY
PET FRIENDLY$1,380 - $1,936/moStudio-2 Beds1-2 BathsLandings at Morrison | 20300 SE Morrison Ter,
Gresham, OR 97030
NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLY
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SENIOR HOUSINGPET FRIENDLYINCOME RESTRICTED
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NEW - 20 HRS AGOSPECIAL OFFERPET FRIENDLYTotal price$1,437 - $1,579/mo1-2 Beds1-2 BathsMountain High Apartments | 1930 SE 6th St,
Gresham, OR 97080
PET FRIENDLY
PET FRIENDLY$1,425 - $1,650/mo1-2 Beds1-2 BathsSpringwater Trail Apartments | 1324 SE Pleasant View Dr,
Gresham, OR 97080
SPECIAL OFFERPET FRIENDLY
PET FRIENDLYINCOME RESTRICTED
PET FRIENDLYINCOME RESTRICTED
PET FRIENDLY
SPECIAL OFFERPET FRIENDLY
NEW - 2 DAYS AGOSPECIAL OFFERPET FRIENDLY
SPECIAL OFFER
PET FRIENDLY$1,450 - $1,875/mo2-3 Beds1-2 BathsDalton Park Apartments | 14201-14205 E Burnside St,
Portland, OR 97233
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NEW - 2 DAYS AGOPET FRIENDLY$1,149 - $1,395/mo1-2 Beds1 BathEastside Village Apartments | 17924 SE Division St,
Portland, OR 97236
SPECIAL OFFERPET FRIENDLY
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SPECIAL OFFERPET FRIENDLYExplore by rental type - Single Family
NEW - 2 HRS AGOPET FRIENDLY
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NEW - 2 DAYS AGOAPPLY INSTANTLYPET FRIENDLY
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APPLY INSTANTLYPET FRIENDLY
Explore by rental type - Townhome
SPECIAL OFFERPET FRIENDLY
NEW - 1 DAY AGOAPPLY INSTANTLYPET FRIENDLY
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APPLY INSTANTLYFURNISHEDROOM FOR RENT
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Explore by feature - Pet Friendly
PET FRIENDLYINCOME RESTRICTED
NEW - 2 DAYS AGOSPECIAL OFFERPET FRIENDLY
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SPECIAL OFFERPET FRIENDLYTotal price$1,316 - $2,573/moStudio-2 bd1-2 baAlta Civic Station | 1699 NW Civic Dr,
Gresham, OR 97030
PET FRIENDLY
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Explore by feature - Air Conditioning
- PET FRIENDLYINCOME RESTRICTED
SPECIAL OFFERINCOME RESTRICTED
PET FRIENDLY
PET FRIENDLYTotal price$1,450 - $1,950/mo1-2 bd1-2 baThe Crossings at Gresham Station | 773 NW 13th St,
Gresham, OR 97030
SPECIAL OFFERPET FRIENDLY
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Explore by feature - Garage
- NEW - 2 DAYS AGOSPECIAL OFFERPET FRIENDLY
- PET FRIENDLY
- PET FRIENDLYTotal price$1,450 - $1,950/mo1-2 bd1-2 baThe Crossings at Gresham Station | 773 NW 13th St,
Gresham, OR 97030 
SPECIAL OFFERPET FRIENDLY
NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLY
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PET FRIENDLY- NEW - 1 DAY AGOAPPLY INSTANTLYPET FRIENDLY
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Explore by rental type - Single Family
- NEW - 2 HRS AGOPET FRIENDLY
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Explore by rental type - Townhome
- SPECIAL OFFERPET FRIENDLY
- NEW - 1 DAY AGOAPPLY INSTANTLYPET FRIENDLY
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- APPLY INSTANTLYFURNISHEDROOM FOR RENT
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Explore by feature - Pet Friendly
- PET FRIENDLYINCOME RESTRICTED
- NEW - 2 DAYS AGOSPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
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- SPECIAL OFFERPET FRIENDLYTotal price$1,316 - $2,573/moStudio-2 bd1-2 baAlta Civic Station | 1699 NW Civic Dr,
Gresham, OR 97030 - PET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
- PET FRIENDLY
- PET FRIENDLY
Explore by feature - Air Conditioning
- PET FRIENDLYINCOME RESTRICTED
- SPECIAL OFFERINCOME RESTRICTED
- PET FRIENDLY
- PET FRIENDLYTotal price$1,450 - $1,950/mo1-2 bd1-2 baThe Crossings at Gresham Station | 773 NW 13th St,
Gresham, OR 97030 - SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
- PET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
- PET FRIENDLY
Explore by feature - Garage
- NEW - 2 DAYS AGOSPECIAL OFFERPET FRIENDLY
- PET FRIENDLY
- PET FRIENDLYTotal price$1,450 - $1,950/mo1-2 bd1-2 baThe Crossings at Gresham Station | 773 NW 13th St,
Gresham, OR 97030 - SPECIAL OFFERPET FRIENDLY
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLY
- PET FRIENDLY
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- NEW - 1 DAY AGOAPPLY INSTANTLYPET 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 Townhomes and Houses.
| 1 bed | 2 beds | 3 beds | 4 beds | All | |
|---|---|---|---|---|---|
| All home types | $1,400 | $1,920 | $1,900 | $2,556 | $1,920 |
| Townhomes | — | — | $2,000 | — | $2,000 |
| Apartments and Condos | $1,400 | $1,820 | — | — | $1,350 |
| Houses | — | $2,400 | $1,900 | $2,556 | $2,000 |
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 $1,842 per month. This is about 6% 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 $1,400 per month. That is about $425 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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