425 High St
ChestertownMD21620
Cheap Apartments for Rent in Chestertown, MD from $500 (18 Rentals)
Search the lowest-cost Apartments available for rent right now in Chestertown.
202 High St
ChestertownMD21620
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from $7701 Bedroom Apartments Available Now
Center Park Apartments
38 Center ParkCentreville, MD 21617
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Rent Specials
from $850Studio to 2 Bedroom Apartments Available Now
Hartland Village Apartments
1103 Country Terrace RdEssex, MD 21221
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from $9191 to 2 Bedroom Apartments Available Now
Kings Mill Apartments and Townhomes
1460 Hadwick DrEssex, MD 21221
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from $940Studio to 2 Bedroom Apartments Available Now
The Greens Apartments and Townhomes
1207 Middleborough RdEssex, MD 21221
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from $9461 to 2 Bedroom Apartments Available Jun 16
Essex Park Apartments and Townhomes
1572 Alconbury RdEssex, MD 21221
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from $9491 to 2 Bedroom Apartments Contact Us For Availability
Brookside Station Apartments
1618 Swallow Crest DrEdgewood, MD 21040
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from $1,0801 to 2 Bedroom Apartments Available Now
Seneca Bay Apartment Homes
3736 White Pine RdMiddle River, MD 21220
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from $1,1271 to 3 Bedroom Apartments Available Now
Beacon Pointe Apartments and Townhomes
7700 Dory LnSparrows Point, MD 21219
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from $1,2001 to 3 Bedroom Apartments Available Now
Hopkins Point by OneWall
37 Alberge LnMiddle River, MD 21220
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6202 Cedar Dr
EdgewoodMD21040
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Chestertown, MD Local Guide
High Street in w:Chestertown, Maryland by Jennifer Schmidt is licensed under Internal
How much does it cost to rent an apartment in Chestertown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chestertown Studio Apartments | $1,141 | $850 | $1,699 |
| Chestertown 1 Bedroom Apartments | $1,553 | $770 | $2,249 |
| Chestertown 2 Bedroom Apartments | $1,817 | $1,039 | $2,700 |
| Chestertown 3 Bedroom Apartments | $1,967 | $1,285 | $2,950 |
| Chestertown 4 Bedroom Apartments | $2,166 | $1,969 | $2,245 |
Browse Top Apartments in Chestertown
See all Apartments in ChestertownExplore Chestertown
Chestertown, MD Local Guide
- Chestertown Neighborhoods
- Nearby Cities
- ZIP codes
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Cheapest Neighborhoods for Apartments in Chestertown, MD
Pricing Updated: 04/13/2025Current apartment rentals in the Chestertown, MD area range in price from to with an overall median price of . Here is today’s list neighborhoods with the lowest median pricing for Chestertown Apartments for rent:
| Neighborhood | Median Price | Min Price | Available Units |
|---|---|---|---|
| Coventry Farms | $1,900 | $1,000 | 5 |
Cheapest Available Chestertown Apartments for Rent and Nearby
The cheapest available apartment rental in Chestertown, MD is a 1 Bed unit found at The Village at Slippery Hill II priced from $585. Center Park Apartments in the North Brook neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $770. Here is today’s list of the most affordable Chestertown apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Village at Slippery Hill II | A1 - One Bedroom Apartment | 1BR,1BA | $585 |
| Center Park Apartments | 1 Bed, 1 bath | 1BR,1BA | $770 |
| Hartland Village Apartments | Studio | Studio,1BA | $850 |
| Kings Mill Apartments and Townhomes | One bedroom Apartment | 1BR,1BA | $919 |
| The Greens Apartments and Townhomes | Studio | Studio,1BA | $940 |
Best Value Apartments for Rent in Chestertown, MD and Nearby
As of April 13, 2025 the best value apartment in the Chestertown area is the $1.39 price per square foot Patriot Village - Patriot Model at Aberdeen Proving Ground on Post Housing in the in the Greenway Farm neighborhood starting from $2,300. The second greatest value Chestertown apartment is the 3 Bedroom 1 Bath Townhouses Ready to Lease! Model at Holly Circle Townhouses starting at $1,650 with a $1.38 price per square foot in the Holly Woods - Woodfield/Wyngate neighborhood. Here is today’s list of the best values for Chestertown apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Aberdeen Proving Ground on Post Housing | Patriot Village - Patriot | 4BR,2.5BA | $1.39 |
| Holly Circle Townhouses | 3 Bedroom 1 Bath Townhouses Ready to Lease! | 3BR,1BA | $1.38 |
| Holly Oaks | 2 Bed 2 Bath | 2BR,2BA | $1.59 |
| Perkins Place | The Garrett | 2BR,1BA | $1.58 |
| The Willows at Cecilton | 2 BEDROOM | 2BR,1BA | $1.10 |
| Seven Oaks Townhomes | 1 Bedroom 1 Bath | 1BR,1BA | $1.69 |
| Kent Crossing Apartments | 1 Bedroom | 1BR,1BA | $1.65 |
| The Village at Slippery Hill II | A1 - One Bedroom Apartment | 1BR,1BA | $0.81 |
| Seneca Bay Apartment Homes | One Bedroom | 1BR,1BA | $1.53 |
| Kings Mill Apartments and Townhomes | One bedroom Apartment | 1BR,1BA | $1.44 |
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Walk Score®
47 / 100
Car-Dependent
Most errands require a car
Bike Score®
55 / 100
Bikeable
Some bike infrastructure
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Cheap Chestertown Apartments
How much is rent for a Cheap One Bedroom Chestertown Apartment?
The lowest price for a Cheap One Bedroom Chestertown Apartment is $585 at The Village at Slippery Hill II.
What is the lowest price for a Cheap Two Bedroom Chestertown Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Chestertown is starting from $1,039 at Kings Mill Apartments and Townhomes.
What is the most affordable Chestertown Three Bedroom Apartment?
The best deal on a cheap Chestertown Three Bedroom Apartment rental is at The Village at Slippery Hill II and starts from $799.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.
Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.
Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.
How Your Move-In Inspection Can Protect Your Security Deposit
Written by: Christine Leonard, Esq.
If you’re anything like most people, housing costs represent a huge chunk of your monthly budget. On top of that, moving can be both a stressful and expensive affair.