Cheap Apartments for Rent in Chester, MD from $1,252 (46 Rentals)

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

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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Bayshore Landing
$1,865 - $2,143
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Total Monthly Price

Base Rent
$1,865 - $2,143
Total Monthly Price
$1,865 - $2,143
1 to 2 Bedroom Apartments Available Now

Bayshore Landing

988 Spa RdAnnapolis, MD 21403
Active Lifestyle
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Maris
Rent Specials
$2,057 - $4,416
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$2,057 - $4,416
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Studio to 2 Bedroom Apartments Available Now

Maris

2445 Holly AveAnnapolis, MD 21401
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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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Aventon Annapolis
Rent Specials
$2,271 - $4,449
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Total Monthly Price

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$2,271 - $4,449
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Studio to 2 Bedroom Apartments Available Now

Aventon Annapolis

2553 Riva RdAnnapolis, MD 21401
Luxury
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Mulberry Estates
1 to 2 Bedroom Apartments

Mulberry Estates

1020-1070 N Washington StEaston, MD 21601
  • 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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Towne Courts
2 to 3 Bedroom Apartments

Towne Courts

100 Francis Noel WayAnnapolis, MD 21401
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Madison Apartments
1 to 2 Bedroom Apartments

Madison Apartments

1000 Madison StAnnapolis, MD 21403
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Americana Southdale
1 to 3 Bedroom Apartments

Americana Southdale

7847 Americana CirGlen Burnie, MD 21060
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West Woods Apartments
1 to 2 Bedroom Apartments

West Woods Apartments

114 Hearne CtAnnapolis, MD 21401
Corporate Housing
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Oakland Hills
Studio to 2 Bedroom Apartments

Oakland Hills

614 Oakland Hills DrArnold, MD 21012
  • 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 1-46, Page 1 of 1

Chester, MD Local Guide

Cheapest Available Chester Apartments for Rent and Nearby

 

The cheapest available apartment rental in Chester, MD is a 1 Bed unit found at The Villages at Marley Station Apartments in the Sloop Cove Landing neighborhood priced from $1,264. The Village at Slippery Hill Senior Apartments- 62+ in the Queen Annes County neighborhood has the second lowest priced unit, which is a 2 Beds apartment currently listed from $1,265. Here is today’s list of the most affordable Chester apartments for rent:

Apartment ListingModel NameBed/BathPriced From
The Villages at Marley Station ApartmentsA21BR,1BA$1,264
The Village at Slippery Hill Senior Apartments- 62+B1 - Two Bedroom2BR,1BA$1,265
Beacon Pointe Apartments and TownhomesA1-1BD/1BA1BR,1BA$1,317
Chatham Village ApartmentsI Bedroom Delux1BR,1BA$1,330
Obery CourtOne Bedroom1BR,1BA$1,389
Americana Southdale1 Bedroom1BR,1BA$1,559
Nautilus PointNautilus | E1 | RenoStudio,1BA$1,592
Harbour Gates ApartmentsStudioStudio,1BA$1,698
Bell Annapolis on WestA1A1BR,1BA$1,770
Bay Manor ApartmentsStudioStudio,1BA$1,850

Best Value Apartments for Rent in Chester, MD and Nearby

As of August 26, 2026 the best value apartment in the Chester area is the $2.05 price per square foot The Schooner Model at The Reserve at Stoney Creek in the in the Pasadena neighborhood starting from $2,770. The second greatest value Chester apartment is the The Marine Model at West Woods Apartments starting at $2,495 with a $1.90 price per square foot in the Monticello neighborhood. Here is today’s list of the best values for Chester apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
The Reserve at Stoney CreekThe Schooner3BR,2BA$2.05
West Woods ApartmentsThe Marine2BR,2BA$1.90
The Promenade at EastonThe Miles3BR,2BA$1.98
Conte Lubrano ApartmentsG2BR,2BA$1.91
Annapolis Roads Apartments2BR 2BA2BR,2BA$2.22
Bay Hills Apartments1B1B1BR,1BA$2.37
The Village at Slippery Hill Senior Apartments- 62+B1 - Two Bedroom2BR,1BA$1.48
Obery CourtOne Bedroom1BR,1BA$1.79
Chatham Village ApartmentsI Bedroom Delux1BR,1BA$2.05
Beacon Pointe Apartments and TownhomesA1-1BD/1BA1BR,1BA$2.20

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

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Frequently Asked Questions about Cheap Chester Apartments

What is the Cheapest Studio apartment in Chester?

Currently the most affordable Cheap Studio Apartment in Chester is at Nautilus Point listed at $1,592.

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

The lowest price for a Cheap One Bedroom Chester Apartment is $1,264 at The Villages at Marley Station Apartments.

What is the lowest price for a Cheap Two Bedroom Chester Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Chester is starting from $1,265 at The Village at Slippery Hill Senior Apartments- 62+.

What is the most affordable Chester Three Bedroom Apartment?

The best deal on a cheap Chester Three Bedroom Apartment rental is at Obery Court and starts from $1,915.

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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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.

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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.