Homes for Rent in Chestertown, MD (35 Rentals)

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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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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

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How a Move-In Inspection Can Protect Your Security Deposit

Learn How a Move-In Inspection Can Protect Your Security Deposit from the Renter University at AparmentHomeLiving.com.

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Showing Results 1-35, Page 1 of 1

Chestertown, MD Local Guide

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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Frequently Asked Questions about Chestertown

What type of rentals are currently available in Chestertown?

There are currently 54 Apartments for Rent in Chestertown, MD with pricing that ranges from $915 to $2,900. There are also 35 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestertown ranging from $1,095 to $3,400.

What is the current price range for Rental Homes in Chestertown?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Chestertown ranges from $1,095 to $3,400 with an average monthly rent of $2,085.

How much are larger Three and Four Bedroom Rentals in Chestertown?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Chestertown range from $1,285 to $2,597, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,600 to $3,400. Four Bedroom Single-Family rentals are also available starting from $2,200 and Four Bedroom Apartments start at $1,899.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.

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Navigating the Rental Market: Tips for First-Time Renters

Written by: Sandy Baker

Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.

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Rise of Digital Nomads: Remote Work Tips for Apartment Renters

Written by: Brandie Parton

As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.