Apartments for Rent in Chestertown, MD (96 Rentals)

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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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321 Calvert St
1 Bedroom Apartments

321 Calvert St

321 Calvert StChestertown, MD 21620
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Baywood Village
1 to 4 Bedroom Apartments

Baywood Village

23160-23165 Baywood CtChestertown, MD 21620
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200 N Queen St
1 to 3 Bedroom Apartments

200 N Queen St

200 N Queen StChestertown, MD 21620
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Upper Shore Aging
Studio Apartments

Upper Shore Aging

402 Morgnec RdChestertown, MD 21620
Senior Living
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121 Washington Ave
1 to 2 Bedroom Apartments

121 Washington Ave

121 Washington AveChestertown, MD 21620
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425 High St
Studio to 2 Bedroom Apartments

425 High St

425 High StChestertown, MD 21620

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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187 Flatland Rd
1 Bedroom Apartments

187 Flatland Rd

187 Flatland RdChestertown, MD 21620

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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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 1-50, Page 1 of 2

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

Explore Chestertown, MD Rentals by Map

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See the most popular apartments and homes in Chestertown, MD

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Getting Around Chestertown, MD

Walk Score®

47 / 100

Car-Dependent

Most errands require a car

Bike Score®

55 / 100

Bikeable

Some bike infrastructure

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about Chestertown

How much are Studio apartments in Chestertown?

There are currently 6 Studio Apartments in Chestertown with rent ranges from $869 to $1,699 with an average price of $1,310.

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 $946 to $2,207 with an average monthly rent of $1,577.

What does renting a Two Bedroom Apartment in Chestertown cost?

The monthly rent prices of Two Bedroom Apartments currently available in Chestertown range from $1,099 to $4,300. Today's average rental price for Two Bedrooms here is $1,765.

How expensive are Chestertown Three Bedroom Apartments?

There are currently 27 Three Bedroom Apartments listings available in Chestertown on ApartmentHomeLiving.com. The pricing ranges from $1,285 to $2,869 - averaging $1,979 for the location.

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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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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The Art of the Rental Viewing: What to look for during a property tour

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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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.