2 Bedroom Apartments for Rent in Chester, MD (52 Rentals)

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Annapolis Bay
Rent Specials
$2,316 - $3,267
Total Monthly Price

Total Monthly Price

Base Rent
$1,927 - $3,756
Required Monthly Fees
$31
Total Monthly Price
$1,958 - $3,787
2 Bedroom Apartments Available Now

Annapolis Bay

721 S Cherry Grove AveAnnapolis, MD 21401
Corporate Housing
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Avalon Annapolis
Rent Specials
$2,925 - $3,210
Total Monthly Price

Total Monthly Price

Base Rent
$2,071 - $3,114
Required Monthly Fees
$96
Total Monthly Price
$2,167 - $3,210
2 Bedroom Apartments Available Now

Avalon Annapolis

2494 Riva RdAnnapolis, MD 21401
Furnished
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Aventon Annapolis
Rent Specials
$3,060 - $3,332
Total Monthly Price

Total Monthly Price

Base Rent
$2,228 - $5,498
Required Monthly Fees
Varies
Total Monthly Price
Varies
2 Bedroom Apartments Available Now

Aventon Annapolis

2553 Riva RdAnnapolis, MD 21401
Luxury
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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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Bayshore Landing
$2,152 - $2,428
Total Monthly Price

Total Monthly Price

Base Rent
$2,002 - $2,428
Total Monthly Price
$2,002 - $2,428
2 Bedroom Apartments Available Now

Bayshore Landing

988 Spa RdAnnapolis, MD 21403
Active Lifestyle
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  • 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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The James
$2,885 - $3,065
Total Monthly Price

Total Monthly Price

Base Rent
$2,051 - $3,918
Required Monthly Fees
$4
Total Monthly Price
$2,055 - $3,922
2 Bedroom Apartments Available Now

The James

251 Admiral Cochrane DrAnnapolis, MD 21401
Furnished
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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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Mulberry Estates
2 Bedroom Apartments

Mulberry Estates

1020-1070 N Washington StEaston, MD 21601
  • Utilities Included
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Madison Apartments
2 Bedroom Apartments

Madison Apartments

1000 Madison StAnnapolis, MD 21403
  • Utilities Included
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Americana Southdale
2 Bedroom Apartments

Americana Southdale

7847 Americana CirGlen Burnie, MD 21060
  • Utilities Included
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Oakland Hills
2 Bedroom Apartments

Oakland Hills

614 Oakland Hills DrArnold, MD 21012
  • Utilities Included
Showing Results 1-50, Page 1 of 2

Chester, MD Local Guide

Largest Available Chester and Nearby 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Chester, MD is found at Mariner Bay at Annapolis Town Center in the Monticello neighborhood and is 1,306 square feet priced from $3,595. Riva Trace Community of Annapolis has the second largest 2 Bedroom, which is sized at 1,285 square feet and currently listed start at $2,200. Here is today’s list of the largest available 2 Bedroom units in Chester:

Apartment ListingModel NameSquare FootagePriced From
Mariner Bay at Annapolis Town Center2 bedroom/2 bath1,306 Sq Ft$3,595
Riva Trace Community of Annapolis2 Bed 2 Bath1,285 Sq Ft$2,200
Aventon AnnapolisB81,275 Sq Ft$3,373
Bell Annapolis on WestB2I1,271 Sq Ft$2,720
Obery CourtTwo Bedroom1,204 Sq Ft$1,400
Bay Manor Apartments2 Bedroom1,196 Sq Ft$2,995
West Woods ApartmentsThe Chester1,193 Sq Ft$2,199
Annapolis Bay2 Bedroom, 2 Bathroom 1,177 SF 22C1,177 Sq Ft$2,485
Avalon AnnapolisB7 - Design Collection II1,167 Sq Ft$3,210
The Promenade at EastonThe Wye1,084 Sq Ft$2,075

Cheapest Available Chester and Nearby 2 Bedroom Apartments

As of March 23, 2026 the lowest priced 2 Bedroom apartment unit in Chester, MD is the B1 - Two Bedroom Model starting from $1,265 at The Village at Slippery Hill Senior Apartments- 62+ . The second most affordable Chester 2 Bedroom is the 2 Bedroom, 1.5 Bathroom - Accessible (Flat) Model at Towne Courts starting at $1,382 in the Monticello neighborhood. The average price for all 2 Bedroom apartments in Chester is currently $2,523. Here is today’s list of the cheapest available 2 Bedroom options in Chester:

Apartment ListingModel NamePriced From
The Village at Slippery Hill Senior Apartments- 62+B1 - Two Bedroom$1,265
Towne Courts2 Bedroom, 1.5 Bathroom - Accessible (Flat)$1,382
Obery CourtTwo Bedroom$1,400
Beacon Pointe Apartments and TownhomesB1-2BD/1BA$1,415
The Villages at Marley Station ApartmentsB1$1,499
Nautilus PointNautilus | B1$1,683
Americana Southdale2 Bedroom$1,699
Quiet Waters LandingB2-2BD/1BA$1,756
Spa Cove ApartmentsChesapeake$1,799
Annapolis Roads Apartments2BR 2BA$2,072

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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

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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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Remember the 3 Rules of Real Estate:
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Frequently Asked Questions about 2 Bedroom Chester Apartments

What is the Cheapest apartment in Chester with 2 Bedroom?

Currently the most affordable 2 Bedroom in Chester is at The Village at Slippery Hill Senior Apartments- 62+ listed at $1,265.

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

The average rent for a 2 Bedroom Apartment in Chester is $2,523.

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

Today's apartment with the most square footage in Chester is a 1,306 square feet unit starting from $3,595 at Mariner Bay at Annapolis Town Center.

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

The average size for a 2 Bedroom rental in Chester is currently 1,027 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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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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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.

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A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.