Cheap Apartments for Rent in Chestertown, MD from $765 (44 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

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Magnolia Farms
1 to 3 Bedroom Apartments

Magnolia Farms

28 E Bel Air AveAberdeen, MD 21001
  • Utilities Included

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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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. Hartland Village Apartments in the Essex neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $937. 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
Hartland Village ApartmentsStudioStudio, 1BA$937
The Greens Apartments and TownhomesStudioStudio, 1BA$937
Kings Mill Apartments and TownhomesOne bedroom Apartment1BR, 1BA$1,065
Hopkins Point by OneWallTwo Bedroom2BR, 1BA$1,075
Hyde Park ApartmentsStudio 1 BathroomStudio, 1BA$1,108
Seneca Bay Apartment HomesOne Bedroom1BR, 1BA$1,155
Middle River Overlook1BD/1BA1BR, 1BA$1,254
Annhurst (MD)Studio 1 Bath OpenStudio, 1BA$1,255
The Village at Slippery Hill Senior Apartments- 62+B1 - Two Bedroom2BR, 1BA$1,265

Best Value Apartments for Rent in Chestertown, MD and Nearby

As of September 20, 2026 the best value apartment in the Chestertown area is the $1.03 price per square foot 3 Bedrooms 1 Bath Model at Foxridge Townhomes in the Essex neighborhood starting from $1,774. The second greatest value Chestertown apartment is the 2 Bed 2 Bath w/ Den Model at Holly Oaks in the Holly Woods - Woodfield/Wyngate neighborhood starting at $2,050 with a $1.61 price per square foot. 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$1.03
Holly Oaks2 Bed 2 Bath w/ Den2BR, 2BA$1.61
Kingston Townhomes3 Bedrooms 1 Bath3BR, 1BA$1.49
Perkins PlaceThe Calvert2BR, 1.5BA$1.76
The Village at Slippery Hill Senior Apartments- 62+B1 - Two Bedroom2BR, 1BA$1.48
Seven Oaks Townhomes1 Bedroom 1 Bath1BR, 1BA$1.73
Hopkins Point by OneWallTwo Bedroom2BR, 1BA$1.41
Seneca Bay Apartment HomesOne Bedroom1BR, 1BA$1.63
Kings Mill Apartments and TownhomesOne bedroom Apartment1BR, 1BA$1.67
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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Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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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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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

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

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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 $937.

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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How Commercial-to-Residential Property Conversions Help the Housing Crisis

Written by: Robin Stewart

Many housing markets throughout America share a common complaint: a lack of affordable rental properties.

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Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

Written by: Robin Stewart

Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.