2 Bedroom Apartments for Rent in Chestertown, MD (51 Rentals)

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121 Washington Ave
2 Bedroom Apartments

121 Washington Ave

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

425 High St

425 High StChestertown, 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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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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The Berkleigh
$2,299 - $2,850
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$1,656 - $3,106
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2 Bedroom Apartments Available Now

The Berkleigh

6221 Greenleigh AveBaltimore, MD 21220
Corporate Housing
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  • Utilities Included
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Arbors Greenleigh
$2,345 - $2,800
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$1,623 - $3,128
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2 Bedroom Apartments Available Now

Arbors Greenleigh

11550 Crossroads CirBaltimore, MD 21220
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  • Utilities Included

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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Enclave at Box Hill
Rent Specials
$2,194 - $2,434
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Total Monthly Price

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$1,710 - $4,287
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2 Bedroom Apartments Available Now

Enclave at Box Hill

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

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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Stansbury Manor
2 Bedroom Apartments

Stansbury Manor

1 Alder DrMiddle River, MD 21220
  • Utilities Included
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 Enclave at Box Hill in the Harford Green neighborhood and is 1,397 square feet priced from $2,266. Harborside Village Apartments in the Goose Pond Estates neighborhood has the second largest 2 Bedroom, which is sized at 1,377 square feet and currently listed start at $2,095. Here is today’s list of the largest available 2 Bedroom units in Chestertown:

Apartment ListingModel NameSquare FootagePriced From
Enclave at Box Hill2 Bed/2 Bath Den-T1,397 Sq Ft$2,266
Harborside Village ApartmentsA3 w/ Den Phase III1,377 Sq Ft$2,095
RiversideThe Driftwood1,313 Sq Ft$2,189
Arbors Greenleigh2 Bed/2 Bath-B3-Hayfield1,218 Sq Ft$2,573
Stansbury Manor2 Bedroom Townhome1,100 Sq Ft$1,874
Aberdeen Proving Ground on Post HousingPatriot Village - Stream1,060 Sq Ft$1,795
ReNew BelcampChesapeake1,050 Sq Ft$1,749
The Berkleigh2 Bed/2 Bath-B1-Bohemia1,046 Sq Ft$2,631
Perkins PlaceThe Calvert1,000 Sq Ft$1,812
Hyde Park ApartmentsTwo Bedroom One Bath967 Sq Ft$1,213

Cheapest Available Chestertown and Nearby 2 Bedroom Apartments

As of April 28, 2026 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 2 Bedroom Model at The Greens Apartments and Townhomes starting at $957 in the Hopewell Point neighborhood. The average price for all 2 Bedroom apartments in Chestertown is currently $1,766. 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
The Greens Apartments and Townhomes2 Bedroom$957
Kings Mill Apartments and TownhomesTwo Bedroom Apartment$1,057
Hopkins Point by OneWallTwo Bedroom$1,075
Hartland Village ApartmentsTwo bedroom$1,106
Essex Park Apartments and TownhomesTwo Bedroom Townhome$1,125
Seneca Bay Apartment HomesTwo Bedroom - 806 sqft$1,170
Hyde Park ApartmentsTwo Bedroom One Bath$1,213
The Village at Slippery Hill Senior Apartments- 62+B1 - Two Bedroom$1,265
Verona at Middle River2BD/1BA$1,299

10 Hidden Costs of Renting You Should Budget for Before Signing a Lease

Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.

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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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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 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.

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

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Frequently Asked Questions about 2 Bedroom Chestertown Apartments

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

The average rent for a 2 Bedroom Apartment in Chestertown is $1,766.

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 $2,266 at 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 1,202 sq ft.

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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Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

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What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Written by: Lauren Harrington

This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

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Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

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

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.