Cheap Apartments for Rent in Chestertown, MD from $500 (38 Rentals)

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

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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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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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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Stansbury Manor
1 to 3 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included

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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Chestertown, MD Local Guide

Cheapest Available Chestertown Apartments for Rent and Nearby

 

The cheapest available apartment rental in Chestertown, MD is a Studio unit found at Hartland Village Apartments in the Hopewell Point neighborhood priced from $677. The Greens Apartments and Townhomes in the Hopewell Point neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $727. Here is today’s list of the most affordable Chestertown apartments for rent:

Apartment ListingModel NameBed/BathPriced From
Hartland Village ApartmentsStudioStudio,1BA$677
The Greens Apartments and TownhomesStudioStudio,1BA$727
Windsor Valley ApartmentsWindsor III- 1 BR, 1 BA1BR,1BA$765
Kings Mill Apartments and TownhomesOne bedroom Apartment1BR,1BA$935
The Village at Slippery Hill Senior Apartments- 62+A3 - One Bedroom1BR,1BA$975
Hyde Park ApartmentsStudio 1 BathroomStudio,1BA$999
Seneca Bay Apartment HomesOne Bedroom1BR,1BA$1,050
Hopkins Point by OneWallTwo Bedroom2BR,1BA$1,075
Annhurst (MD)One Bed One Bath Standard1BR,1BA$1,225
Chesapeake Village Apartments1 Bedroom, 1 Bath1BR,1BA$1,247

Best Value Apartments for Rent in Chestertown, MD and Nearby

As of May 07, 2026 the best value apartment in the Chestertown area is the $1.45 price per square foot 3 Bedrooms 1.5 Bath Model at Seven Oaks Townhomes in the in the Goose Pond Estates neighborhood starting from $1,750. The second greatest value Chestertown apartment is the 3 Bedrooms 1 Bath Model at Kingston Townhomes starting at $1,683 with a $1.53 price per square foot in the Miramar Landing - Gibson/Taylor 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.
Seven Oaks Townhomes3 Bedrooms 1.5 Bath3BR,1.5BA$1.45
Kingston Townhomes3 Bedrooms 1 Bath3BR,1BA$1.53
Harborside Village ApartmentsUnit B Waterview - Phase II1BR,1BA$1.78
Kings Mill Apartments and TownhomesTwo Bedroom Townhome2BR,1BA$1.65
Hopkins Point by OneWallTwo Bedroom2BR,1BA$1.41
Verona at Middle River2BD/1BA2BR,1BA$1.80
Seneca Bay Apartment HomesOne Bedroom - 629 sqft1BR,1BA$1.67
The Village at Slippery Hill Senior Apartments- 62+A5 - One Bedroom1BR,1BA$1.69
Hyde Park ApartmentsStudio 1 BathroomStudio ,1BA$1.60
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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Quick Rent Budget Calculator

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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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 $677.

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

decorative image for A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back article

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Written by: Lauren Harrington

I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

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Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

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

Written by: Lauren Harrington

This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

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Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.