2 Bedroom Apartments for Rent in Chestertown, MD (55 Rentals)

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425 High St
2 Bedroom Apartments

425 High St

425 High StChestertown, MD 21620
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121 Washington Ave
2 Bedroom Apartments

121 Washington Ave

121 Washington AveChestertown, MD 21620
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Baywood Village
2 Bedroom Apartments

Baywood Village

23160-23165 Baywood CtChestertown, MD 21620

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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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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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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Showing Results 1-50, Page 1 of 2

Chestertown, MD Local Guide

Largest Available Chestertown and Nearby 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Chestertown, MD is found at The Enclave at Box Hill in the Harford Green neighborhood and is 1,397 square feet priced from $2,441. Harborside Village Apartments in the Goose Pond Estates neighborhood has the second largest 2 Bedroom, which is sized at 1,341 square feet and currently listed start at $1,995. Here is today’s list of the largest available 2 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
The Enclave at Box Hill2 Bed/2 Bath Den-T1,397 Sq Ft$2,441
Harborside Village ApartmentsG3 w/ Sunroom - Phase III1,341 Sq Ft$1,995
Riverside2 Bedroom 2 Bath - D1,313 Sq Ft$2,019
Arbors Greenleigh2 Bed/2 Bath Loft-B2L-Levere1,277 Sq Ft$2,400
The Berkleigh2 Bed/2 Bath-B4-Dundee1,266 Sq Ft$2,650
ReNew BelcampCamden1,200 Sq Ft$1,899
Perkins PlaceThe Garrett1,125 Sq Ft$1,739
Stansbury Manor2 Bedroom Townhome1,100 Sq Ft$1,899
Aberdeen Proving Ground on Post HousingPatriot Village - Stream1,060 Sq Ft$1,895
The Willows at Cecilton2 BEDROOM935 Sq Ft$1,156

Cheapest Available Chestertown and Nearby 2 Bedroom Apartments

As of November 22, 2025 the lowest priced 2 Bedroom apartment unit in Chestertown, MD is the Windsor III- 2 BR, 1 BA Model starting from $950 at Windsor Valley Apartments in the Goose Pond Estates neighborhood. The second most affordable Chestertown 2 Bedroom is the Two Bedroom Apartment Model at Kings Mill Apartments and Townhomes starting at $1,149 in the Miramar Landing - Gibson/Taylor neighborhood. The average price for all 2 Bedroom apartments in Chestertown is currently $1,807. Here is today’s list of the cheapest available 2 Bedroom options in Chestertown:

Apartment ListingModel NamePriced From
Windsor Valley ApartmentsWindsor III- 2 BR, 1 BA$950
Kings Mill Apartments and TownhomesTwo Bedroom Apartment$1,149
The Willows at Cecilton2 BEDROOM$1,156
Hyde Park ApartmentsTwo Bedroom One Bath$1,184
The Greens Apartments and Townhomes2 Bedroom$1,208
Hartland Village ApartmentsTwo bedroom$1,231
Hopkins Point by OneWallTwo Bedroom$1,250
The Village at Slippery Hill Senior Apartments- 62+B1 - Two Bedroom$1,265
Verona at Middle RiverSicily$1,324
Seneca Bay Apartment HomesTwo Bedroom - 806 sqft$1,325

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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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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

Explore Chestertown, MD Rentals by Map

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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 2 Bedroom Chestertown Apartments

What is the Cheapest apartment in Chestertown with 2 Bedroom?

Currently the most affordable 2 Bedroom in Chestertown is at Windsor Valley Apartments listed at $950.

How much is the average rent for a 2 Bedroom Chestertown Apartment?

The average rent for a 2 Bedroom Apartment in Chestertown is $1,807.

What is the largest available 2 Bedroom Chestertown Apartment for rent?

Today's apartment with the most square footage in Chestertown is a 1,397 square feet unit starting from $2,441 at The Enclave at Box Hill.

What is the average size for Chestertown 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Chestertown is currently 1,081 sq ft.

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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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.