Chestertown, MD Apartments For Rent
20,227 rentals
Use arrow keys to navigatePET FRIENDLYThe Bozzuto Group
Use arrow keys to navigateNEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYUDR
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLYFURNISHEDJersey Central Management
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLYJersey Central Management
Use arrow keys to navigatePET FRIENDLY
Use arrow keys to navigateNEW - 2 DAYS AGOPET FRIENDLYURL Management LLC
Use arrow keys to navigatePET FRIENDLYTotal price$2,810 - $3,900/mo
1-2 Beds
1-2 BathsThe Monarch | 92-33 Guy R Brewer Blvd,
Jamaica, NY 11433
NEW - 1 DAY AGOPET FRIENDLYBrookfield Properties
PET FRIENDLYWindsor Communities
SPECIAL OFFERPET FRIENDLYTotal price$2,606 - $5,756/moStudio-2 Beds1-2 BathsThird at Bankside | 2385 3rd Ave,
Bronx, NY 10451Brookfield Properties
SPECIAL OFFERPET FRIENDLYBrookfield Properties
SPECIAL OFFERPET FRIENDLYROOM FOR RENT
PET FRIENDLY$2,850 - $3,400/moStudio-1 Bed1 BathThe Tides At Arverne By The Sea | 190 Beach 69th St,
Arverne, NY 11692Beechwood Homes
PET FRIENDLY$2,815 - $5,950/moStudio-2 Beds1-2 BathsThe Residences at Lighthouse Point | 5 Bay St,
Staten Island, NY 10301
SPECIAL OFFERPET FRIENDLYBrookfield Properties
NEW - 1 DAY AGOSPECIAL OFFERTotal price$3,576 - $7,154/mo1-2 Beds1-2 BathsHearthstone Astoria | 34-35 44th St,
Long Island City, NY 11101Greystar
PET FRIENDLY
PET FRIENDLYFURNISHEDUDR
PET FRIENDLYTotal price$3,383 - $7,587/moStudio-2 Beds1-2 BathsWilloughby | 196 Willoughby St,
Brooklyn, NY 11201The Bozzuto Group
NEW - 1 DAY AGOPET FRIENDLYBrookfield Properties
SPECIAL OFFERPET FRIENDLYGreystar
NEW - 1 DAY AGOPET FRIENDLYThe Bozzuto Group
NEW - 1 DAY AGOPET FRIENDLYRealty Operations Group
NEW - 2 DAYS AGOPursuitAgency
NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYTotal price$4,473 - $10,365/moStudio-2 Beds1-2 BathsThe Sagamore | 189 W 89th St,
New York, NY 10024Greystar
PET FRIENDLYThe Bozzuto Group
SPECIAL OFFER
SPECIAL OFFERPET FRIENDLYGreystar
SPECIAL OFFERPET FRIENDLYFURNISHEDGreystar
PET FRIENDLYFURNISHED
SPECIAL OFFERPET FRIENDLYFURNISHEDUDR
SPECIAL OFFERPET FRIENDLYBrookfield Properties
NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYGreystar
SPECIAL OFFERPET FRIENDLYGreystar
PET FRIENDLYWindsor Communities
SPECIAL OFFERPET FRIENDLYBrookfield PropertiesExplore by rental type - Single Family
NEW - 35 MIN AGOAPPLY INSTANTLY
NEW - 5 HRS AGOAPPLY INSTANTLYREAL BROKER LLC
NEW - 7 HRS AGOAPPLY INSTANTLYE-Realty International Corp
NEW - 8 HRS AGOAPPLY INSTANTLYFURNISHED
NEW - 8 HRS AGOAPPLY INSTANTLYEXP Realty
NEW - 11 HRS AGOPET FRIENDLYFURNISHEDBen Bay Realty Co
NEW - 14 HRS AGOAPPLY INSTANTLYUnited National Realty
NEW - 20 HRS AGOAPPLY INSTANTLYTiffany Moves You, Inc.
Explore by rental type - Townhome
NEW - 1 DAY AGOAPPLY INSTANTLY
NEW - 50 MIN AGOAPPLY INSTANTLYPET FRIENDLY
NEW - 7 HRS AGOAPPLY INSTANTLYRental Professionals Inc
NEW - 1 DAY AGOAPPLY INSTANTLYHT Realty Group (DBA for Han Tang Realty Inc.)
NEW - 2 DAYS AGOAPPLY INSTANTLYWinzone Realty, Inc.
APPLY INSTANTLYHT Realty Group (DBA for Han Tang Realty Inc.)
NEW - 2 DAYS AGOAPPLY INSTANTLYPET FRIENDLYHT Realty Group (DBA for Han Tang Realty Inc.)
APPLY INSTANTLYPET FRIENDLYFURNISHED
APPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLYPET FRIENDLYVoro Real Estate
Explore by rental type - Condo
NEW - 1 DAY AGOBERKSHIRE HATHAWAY
PET FRIENDLYTru International Realty Corp
PET FRIENDLYTru International Realty Corp
Explore by feature - Pet Friendly
SPECIAL OFFERPET FRIENDLYGreystar
PET FRIENDLYBaron Residential
PET FRIENDLYWindsor Communities
SPECIAL OFFERPET FRIENDLYThe Bozzuto Group
NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYUDR
SPECIAL OFFERPET FRIENDLY
SPECIAL OFFERPET FRIENDLY
NEW - 1 DAY AGOPET FRIENDLY
PET FRIENDLYOnline Marketing Group
Explore by feature - Air Conditioning
- PET FRIENDLYWindsor Communities
- SPECIAL OFFERPET FRIENDLYThe Bozzuto Group
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYUDR
NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYStrategy Media Services
SPECIAL OFFERPET FRIENDLYGreystar
SPECIAL OFFERPET FRIENDLYEquity Residential
NEW - 1 DAY AGOPET FRIENDLYThe Bozzuto Group
FURNISHEDROOM FOR RENT
Explore by feature - Garage
- PET FRIENDLYWindsor Communities
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYUDR
NEW - 1 DAY AGOPET FRIENDLYBrookfield Properties- SPECIAL OFFERPET FRIENDLYEquity Residential
PET FRIENDLYThe Bozzuto Group
SPECIAL OFFERPET FRIENDLYThe Bozzuto Group
PET FRIENDLY
SPECIAL OFFERPET FRIENDLYINCOME RESTRICTEDHeller Organization
Explore by rental type - Single Family
- NEW - 35 MIN AGOAPPLY INSTANTLY
- NEW - 5 HRS AGOAPPLY INSTANTLYREAL BROKER LLC
- NEW - 7 HRS AGOAPPLY INSTANTLYE-Realty International Corp
- NEW - 8 HRS AGOAPPLY INSTANTLYFURNISHED
- NEW - 8 HRS AGOAPPLY INSTANTLYEXP Realty
- NEW - 11 HRS AGOPET FRIENDLYFURNISHEDBen Bay Realty Co
- NEW - 14 HRS AGOAPPLY INSTANTLYUnited National Realty
- NEW - 20 HRS AGOAPPLY INSTANTLYTiffany Moves You, Inc.
Explore by rental type - Townhome
- NEW - 1 DAY AGOAPPLY INSTANTLY
- NEW - 50 MIN AGOAPPLY INSTANTLYPET FRIENDLY
- NEW - 7 HRS AGOAPPLY INSTANTLYRental Professionals Inc
- NEW - 1 DAY AGOAPPLY INSTANTLYHT Realty Group (DBA for Han Tang Realty Inc.)
- NEW - 2 DAYS AGOAPPLY INSTANTLYWinzone Realty, Inc.
- APPLY INSTANTLYHT Realty Group (DBA for Han Tang Realty Inc.)
- NEW - 2 DAYS AGOAPPLY INSTANTLYPET FRIENDLYHT Realty Group (DBA for Han Tang Realty Inc.)
- APPLY INSTANTLYPET FRIENDLYFURNISHED
- APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLYVoro Real Estate
Explore by rental type - Condo
- NEW - 1 DAY AGOBERKSHIRE HATHAWAY
- PET FRIENDLYTru International Realty Corp
- PET FRIENDLYTru International Realty Corp
Explore by feature - Pet Friendly
- SPECIAL OFFERPET FRIENDLYGreystar
- PET FRIENDLYBaron Residential
- PET FRIENDLYWindsor Communities
- SPECIAL OFFERPET FRIENDLYThe Bozzuto Group
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYUDR
- SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
- NEW - 1 DAY AGOPET FRIENDLY
- PET FRIENDLYOnline Marketing Group
Explore by feature - Air Conditioning
- PET FRIENDLYWindsor Communities
- SPECIAL OFFERPET FRIENDLYThe Bozzuto Group
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYUDR
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYStrategy Media Services
- SPECIAL OFFERPET FRIENDLYGreystar
- SPECIAL OFFERPET FRIENDLYEquity Residential
- NEW - 1 DAY AGOPET FRIENDLYThe Bozzuto Group
- FURNISHEDROOM FOR RENT
Explore by feature - Garage
- PET FRIENDLYWindsor Communities
- NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLYUDR
- NEW - 1 DAY AGOPET FRIENDLYBrookfield Properties
- SPECIAL OFFERPET FRIENDLYEquity Residential
- PET FRIENDLYThe Bozzuto Group
- SPECIAL OFFERPET FRIENDLYThe Bozzuto Group
- PET FRIENDLY
- SPECIAL OFFERPET FRIENDLYINCOME RESTRICTEDHeller Organization
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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