Cheap Apartments for Rent in Chestertown, MD from $500 (42 Rentals)

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Search the lowest-cost Apartments available for rent right now in Chestertown.

Rent According to Income: A Look at Income-Restricted Rentals

Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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Merion Village
1 to 2 Bedroom Apartments

Merion Village

904 Edgewood RdEdgewood, MD 21040
Senior Living

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

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Stansbury Manor
1 to 3 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

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Showing Results 1-42, Page 1 of 1

Chestertown, MD Local Guide

Cheapest Available Chestertown Apartments for Rent and Nearby

 

The cheapest available apartment rental in Chestertown, MD is a 1 Bed unit found at Windsor Valley Apartments in the Goose Pond Estates neighborhood priced from $765. The Greens Apartments and Townhomes in the Essex neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $897. Here is today’s list of the most affordable Chestertown apartments for rent:

Apartment ListingModel NameBed/BathPriced From
Windsor Valley ApartmentsWindsor III- 1 BR, 1 BA1BR,1BA$765
The Greens Apartments and TownhomesStudioStudio,1BA$897
Hartland Village ApartmentsStudioStudio,1BA$897
Hyde Park ApartmentsStudio 1 BathroomStudio,1BA$1,013
The Village at Slippery Hill Senior Apartments- 62+A5 - One Bedroom1BR,1BA$1,080
Kings Mill Apartments and TownhomesOne bedroom Apartment1BR,1BA$1,118
Merion Village1 Bedroom 1 Bath1BR,1BA$1,135
Middle River Overlook2BD/1BA2BR,1BA$1,135
Magnolia Farms2 Bedroom Apt2BR,1BA$1,190
Seneca Bay Apartment HomesTwo Bedroom - 806 sqft2BR,1BA$1,240

Best Value Apartments for Rent in Chestertown, MD and Nearby

As of August 06, 2026 the best value apartment in the Chestertown area is the $1.00 price per square foot 3 Bedrooms 1 Bath Model at Foxridge Townhomes in the in the Essex neighborhood starting from $1,723. The second greatest value Chestertown apartment is the 3 bedroom 3 bathrooms Model at Carriage Court Apartments starting at $1,600 with a $1.10 price per square foot in the Trimble Meadows neighborhood. Here is today’s list of the best values for Chestertown apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
Foxridge Townhomes3 Bedrooms 1 Bath3BR,1BA$1.00
Carriage Court Apartments3 bedroom 3 bathrooms3BR,2BA$1.10
Holly Oaks3 Bed 2 Bath3BR,2BA$1.62
Kingston Townhomes3 Bedrooms 1 Bath3BR,1BA$1.51
Seneca Bay Apartment HomesTwo Bedroom - 853 sqft2BR,1BA$1.48
Magnolia Farms2 Bedroom Apt2BR,1BA$1.40
Merion Village1 Bedroom 1 Bath1BR,1BA$1.44
Middle River Overlook2BD/1BA2BR,1BA$1.58
Hyde Park ApartmentsStudio 1 BathroomStudio ,1BA$1.62
Windsor Valley ApartmentsWindsor I & II- 1 BR, 1 BA1BR,1BA$1.36

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Pet Friendly Lifestyle

Ranked #

Among cities in Maryland for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

Pet Friendly

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Chestertown, MD Rentals by Map

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See the most popular apartments and homes in Chestertown, MD

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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 $897.

How much is rent for a Cheap One Bedroom Chestertown Apartment?

The lowest price for a Cheap One Bedroom Chestertown Apartment is $765 at Windsor Valley 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 $950 at Windsor Valley Apartments.

What is the most affordable Chestertown Three Bedroom Apartment?

The best deal on a cheap Chestertown Three Bedroom Apartment rental is at Windsor Valley Apartments and starts from $1,050.

Expert Rental Resources

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.

Articles, How-To's, and Tips

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Rent According to Income: A Look at Income-Restricted Rentals

Written by: Robin Stewart

The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.