Chestertown, MD Apartments For Rent
94 rentals
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLYTotal price$1,542 - $1,988/mo
1-3 Beds
1-2 BathsSunscapes | 327 Floral Beach Way #6-305,
Myrtle Beach, SC 29575
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLY$1,649 - $1,999/mo3 Beds3 BathsSurfside Retreat | 171 Eagles Cliff Dr #139383,
Myrtle Beach, SC 29575
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- PET FRIENDLY
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- PET FRIENDLY
- APPLY INSTANTLYROOM FOR RENT
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- APPLY INSTANTLY
- APPLY INSTANTLYPET FRIENDLYFURNISHED
- APPLY INSTANTLYPET FRIENDLYFURNISHED
- APPLY INSTANTLYPET FRIENDLY
- PET FRIENDLY
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- NEW - 1 DAY AGOAPPLY INSTANTLYFURNISHED
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- APPLY INSTANTLY
- APPLY INSTANTLYPET FRIENDLY
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- APPLY INSTANTLY
- APPLY INSTANTLYFURNISHED
- APPLY INSTANTLYFURNISHED
- APPLY INSTANTLYFURNISHED
Explore by feature - Pet Friendly
- APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLYROOM FOR RENT
- APPLY INSTANTLYPET FRIENDLYFURNISHED
- APPLY INSTANTLYPET FRIENDLY
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Explore by feature - Garage
- APPLY INSTANTLY
- APPLY INSTANTLYROOM FOR RENT
- APPLY INSTANTLYFURNISHED
- APPLY INSTANTLYPET FRIENDLYFURNISHED
- APPLY 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 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 Townhomes and Houses.
| 1 bed | 2 beds | 3 beds | 4 beds | All | |
|---|---|---|---|---|---|
| All home types | $1,500 | $1,700 | $2,600 | $2,500 | $2,050 |
| Townhomes | — | — | $2,095 | — | $2,095 |
| Apartments and Condos | $1,500 | $1,700 | — | — | $1,520 |
| Houses | — | — | $2,600 | $2,500 | $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.
- What is the average rent of a townhome in Chestertown, MD?The average rent of a townhome in Chestertown, MD is $2,095 per month. This is about 7% 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.