Apartments for Rent in Chester, MD (92 Rentals)

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property at 190 Harrier Wy

$4,000

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Base Rent
$4,000
Total Monthly Price
$4,000

3 Bedroom, 3 Bath Condo for Rent

Available Now

190 Harrier Wy, Unit 24

190 Harrier Wy
ChesterMD21619
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Maris
Rent Specials
$2,050 - $4,416
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Total Monthly Price

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$2,050 - $4,416
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Studio to 2 Bedroom Apartments Available Now

Maris

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

Total Monthly Price

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

Aventon Annapolis

2553 Riva RdAnnapolis, MD 21401
Luxury
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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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Bayshore Landing
$1,865 - $2,143
Total Monthly Price

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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Neighborhood & Market Insights: How to Choose the Right Area to Rent

Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

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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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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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Chester, MD Local Guide

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

Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.

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

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Frequently Asked Questions about Chester

What is the current pricing and availability for apartments for rent in Chester, MD?

As of today, August 26, 2026, there are currently 92 available Chester apartments priced from $1,252 to $6,482, with an average monthly rent of $2,412.

How much are Studio apartments in Chester?

There are currently 12 Studio Apartments in Chester with rent ranges from $1,593 to $2,860 with an average price of $2,189.

What is the current price range for One Bedroom Chester Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Chester ranges from $1,252 to $4,568 with an average monthly rent of $2,199.

What does renting a Two Bedroom Apartment in Chester cost?

The monthly rent prices of Two Bedroom Apartments currently available in Chester range from $1,409 to $6,182. Today's average rental price for Two Bedrooms here is $2,663.

How expensive are Chester Three Bedroom Apartments?

There are currently 26 Three Bedroom Apartments listings available in Chester on ApartmentHomeLiving.com. The pricing ranges from $1,915 to $6,482 - averaging $2,933 for the location.

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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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.

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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.