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Cheap Apartments for Rent in Chestertown, MD from $500 (16 Rentals)
Search the lowest-cost Apartments available for rent right now in Chestertown.
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Rent Specials
from $869Studio to 2 Bedroom Apartments Available Now
Hartland Village Apartments
1103 Country Terrace RdEssex, MD 21221
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Rent Specials
from $938Studio to 2 Bedroom Apartments Available Jul 26
Hyde Park Apartments
1114 Tace DrEssex, MD 21221
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Rent Specials
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 Sep 19
Essex Park Apartments and Townhomes
1572 Alconbury RdEssex, MD 21221
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
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Rent Specials
from $1,0381 to 2 Bedroom Apartments Available Now
Kings Mill Apartments and Townhomes
1460 Hadwick DrEssex, MD 21221
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from $1,0851 to 2 Bedroom Apartments Available Now
Perryman Station Senior Apartments, 62+
1222 Perryman RdAberdeen, MD 21001
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from $1,0851 to 2 Bedroom Apartments Available Now
Seneca Bay Apartment Homes
3736 White Pine RdMiddle River, MD 21220
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The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
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6202 Cedar Dr
EdgewoodMD21040
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
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6203 Edgewood Rd
EdgewoodMD21040
Showing Results 1-16, Page 1 of 1
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 | $1,384 | $869 | $1,699 |
| Chestertown 1 Bedroom Apartments | $1,567 | $946 | $2,281 |
| Chestertown 2 Bedroom Apartments | $1,743 | $1,039 | $2,900 |
| Chestertown 3 Bedroom Apartments | $1,939 | $1,285 | $2,622 |
| Chestertown 4 Bedroom Apartments | $2,125 | $1,949 | $2,245 |
Browse Top Apartments in Chestertown
See all Apartments in ChestertownExplore Chestertown
Chestertown, MD Local Guide
- Chestertown Neighborhoods
- Nearby Cities
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Cheapest Neighborhoods for Apartments in Chestertown, MD
Pricing Updated: 07/14/2025Current 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 | $1,300 | 3 |
Cheapest Available Chestertown Apartments for Rent and Nearby
The cheapest available apartment rental in Chestertown, MD is a 3 Beds unit found at The Village at Slippery Hill II priced from $799. Hartland Village Apartments in the Hopewell Point neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $869. 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 | C2 - Three Bedroom Townhome | 3BR,2BA | $799 |
| Hartland Village Apartments | Studio | Studio,1BA | $869 |
| The Greens Apartments and Townhomes | Studio | Studio,1BA | $940 |
| Kings Mill Apartments and Townhomes | One bedroom Apartment | 1BR,1BA | $1,038 |
| Perryman Station Senior Apartments, 62+ | 1 bedroom | 1BR,1BA | $1,085 |
Best Value Apartments for Rent in Chestertown, MD and Nearby
As of July 14, 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 C3 - Three Bedroom Townhome Model at The Village at Slippery Hill II starting at $1,120 with a $0.78 price per square foot . 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 |
| The Village at Slippery Hill II | C3 - Three Bedroom Townhome | 3BR,2BA | $0.78 |
| Holly Circle Townhouses | 3 Bed 1.5 Bath | 3BR,1.5BA | $1.32 |
| Holly Oaks | 2 Bed 2 Bath | 2BR,2BA | $1.58 |
| Carriage Court Apartments | 3 bedroom 2 bathrooms | 3BR,2BA | $1.27 |
| Kent Crossing Apartments | Mingles 2 Bedroom | 2BR,2BA | $1.57 |
| The Willows at Cecilton | 2 BEDROOM | 2BR,1BA | $1.10 |
| Seven Oaks Townhomes | 2 Bedrooms 1.5 Bath | 2BR,1.5BA | $1.52 |
| Seneca Bay Apartment Homes | One Bedroom | 1BR,1BA | $1.54 |
| Kings Mill Apartments and Townhomes | One bedroom Apartment | 1BR,1BA | $1.62 |
Quick Rent Budget Calculator
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Chestertown, MD Apartments MapChestertown, MD Rental Homes MapGetting Around Chestertown, MD
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
What is the Cheapest Studio apartment in Chestertown?
Currently the most affordable Cheap Studio Apartment in Chestertown is at Hartland Village Apartments listed at $869.
How much is rent for a Cheap One Bedroom Chestertown Apartment?
The lowest price for a Cheap One Bedroom Chestertown Apartment is $986 at Hartland Village Apartments.
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 $1,143 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.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.
The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.
Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.
The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.