Apartments for Rent in Chestertown, MD (92 Rentals)

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property at 351 Calvert St

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000
Total Monthly Price
$2,000

3 Bedroom, 1 Bath Townhome for Rent

Available Now

351 Calvert St

ChestertownMD21620

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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Arbors Greenleigh
$1,623 - $2,973
Total Monthly Price

Total Monthly Price

Base Rent
$1,623 - $2,973
Total Monthly Price
$1,623 - $2,973
1 to 3 Bedroom Apartments Available Now

Arbors Greenleigh

11550 Crossroads CirBaltimore, MD 21220
Family Friendly
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  • Customer Reviewed
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The Berkleigh
$1,921 - $2,855
Total Monthly Price

Total Monthly Price

Base Rent
$1,921 - $2,855
Total Monthly Price
$1,921 - $2,855
Studio to 3 Bedroom Apartments Available Now

The Berkleigh

6221 Greenleigh AveBaltimore, MD 21220
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour

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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Enclave at Box Hill
Rent Specials
$1,839 - $6,023
Total Monthly Price

Total Monthly Price

Base Rent
$1,839 - $6,023
Total Monthly Price
Varies
1 to 3 Bedroom Apartments Available Now

Enclave at Box Hill

3405 McCurley DrAbingdon, MD 21009
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour

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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Chestertown, 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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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 Chestertown

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

As of today, July 30, 2026, there are currently 92 available Chestertown apartments priced from $765 to $3,707, with an average monthly rent of $1,698.

What Chestertown neighborhoods have the most available apartments?

There are 1 neighborhoods in the Chestertown area with available listings as of today. The three neighborhoods with the most options are Miramar Landing - Woodfield/Wyngate with 99 listings, Miramar Landing - Gibson/Taylor with 99 listings, and Middle River Baltimore Crossroads with 99 listings.

How much are Studio apartments in Chestertown?

There are currently 7 Studio Apartments in Chestertown with rent ranges from $897 to $1,260 with an average price of $1,026.

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

Today's rental pricing for One Bedroom Apartments in Chestertown ranges from $765 to $2,256 with an average monthly rent of $1,604.

What does renting a Two Bedroom Apartment in Chestertown cost?

The monthly rent prices of Two Bedroom Apartments currently available in Chestertown range from $950 to $2,855. Today's average rental price for Two Bedrooms here is $1,678.

How expensive are Chestertown Three Bedroom Apartments?

There are currently 32 Three Bedroom Apartments listings available in Chestertown on ApartmentHomeLiving.com. The pricing ranges from $1,050 to $3,707 - averaging $2,005 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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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.

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

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

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.