2 Bedroom Apartments for Rent in Chester, MD (59 Rentals)

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Renting with Roommates: Realistic Expectations for Shared Lease

Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

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Maris
Rent Specials
$2,797 - $2,907
Total Monthly Price

Total Monthly Price

Base Rent
$1,873 - $4,702
Total Monthly Price
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2 Bedroom Apartments Available Jun 2

Maris

2445 Holly AveAnnapolis, MD 21401
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Aventon Annapolis
Rent Specials
$2,929 - $3,029
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$2,254 - $5,091
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Aventon Annapolis

2553 Riva RdAnnapolis, MD 21401
Luxury
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Bayshore Landing
$2,222 - $2,783
Total Monthly Price

Total Monthly Price

Base Rent
$1,818 - $2,783
Total Monthly Price
$1,818 - $2,783
2 Bedroom Apartments Available Now

Bayshore Landing

988 Spa RdAnnapolis, MD 21403
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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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Stone Point Apartments
Rent Specials
$2,860 - $3,149
Total Monthly Price

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$2,223 - $4,774
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2 Bedroom Apartments Available Now

Stone Point Apartments

116 Stone Point DrAnnapolis, MD 21401
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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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Gardens of Annapolis
Rent Specials
$2,893 - $3,700
Total Monthly Price

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$2,395 - $3,700
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2 Bedroom Apartments Available Now

Gardens of Annapolis

931 Edgewood RdAnnapolis, MD 21403
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Renting Smart: Lease Basics Every Renter Needs

Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

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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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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 Creekstone Village Apartments in the Sloop Cove Landing neighborhood and is 1,370 square feet priced from $2,568. Mariner Bay at Annapolis Town Center in the Monticello neighborhood has the second largest 2 Bedroom, which is sized at 1,306 square feet and currently listed start at $3,677. Here is today’s list of the largest available 2 Bedroom units in Chester:

Apartment ListingModel NameSquare FootagePriced From
Creekstone Village ApartmentsG1_CF1,370 Sq Ft$2,568
Mariner Bay at Annapolis Town Center2 bedroom/2 bath1,306 Sq Ft$3,677
Riva Trace Community of Annapolis2 Bed 2 Bath1,285 Sq Ft$2,200
Stone Point ApartmentsCape May (w/loft)1,274 Sq Ft$3,308
Obery CourtTwo Bedroom1,204 Sq Ft$1,400
Bay Manor Apartments2 Bedroom1,196 Sq Ft$2,995
Aventon AnnapolisB61,167 Sq Ft$3,067
Avalon AnnapolisB3 - Design Collection II - Apt 11231,148 Sq Ft$2,945
The JamesB2D1,120 Sq Ft$3,130
The Promenade at EastonThe Wye1,084 Sq Ft$1,999

Cheapest Available Chester and Nearby 2 Bedroom Apartments

As of May 08, 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 B1-2BD/1BA Model at Beacon Pointe Apartments and Townhomes starting at $1,315 in the Evergreen Park Holly Beach neighborhood. The average price for all 2 Bedroom apartments in Chester is currently $2,569. 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
Beacon Pointe Apartments and TownhomesB1-2BD/1BA$1,315
Obery CourtTwo Bedroom$1,400
The Villages at Marley Station ApartmentsB1$1,499
Americana Southdale2 Bedroom$1,649
Nautilus PointNautilus | B1$1,705
Quiet Waters LandingB1-2BD/1BA$1,795
Spa Cove ApartmentsChesapeake$1,873
The Promenade at EastonThe Wye$1,999
Harbour Gates Apartments2 Bedrooms + 1 Bath$2,088

Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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Frequently Asked Questions about 2 Bedroom Chester Apartments

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

The average rent for a 2 Bedroom Apartment in Chester is $2,569.

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

Today's apartment with the most square footage in Chester is a 1,370 square feet unit starting from $2,568 at Creekstone Village Apartments.

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

The average size for a 2 Bedroom rental in Chester is currently 1,259 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.

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Maximizing Your Refund: Essential Tax Tips for Renters

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