2 Bedroom Apartments for Rent in Chester, MD (54 Rentals)

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Maris
Rent Specials
$2,926 - $3,091
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Base Rent
$1,949 - $4,510
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2 Bedroom Apartments Available Now

Maris

2445 Holly AveAnnapolis, MD 21401
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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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Aventon Annapolis
Rent Specials
$3,092 - $3,322
Total Monthly Price

Total Monthly Price

Base Rent
$2,261 - $4,486
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2 Bedroom Apartments Available Now

Aventon Annapolis

2553 Riva RdAnnapolis, MD 21401
Luxury
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Bayshore Landing
$2,221 - $2,499
Total Monthly Price

Total Monthly Price

Base Rent
$1,698 - $2,499
Total Monthly Price
$1,698 - $2,499
2 Bedroom Apartments Available Aug 15

Bayshore Landing

988 Spa RdAnnapolis, MD 21403
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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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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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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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Mulberry Estates
2 Bedroom Apartments

Mulberry Estates

1020-1070 N Washington StEaston, MD 21601
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Towne Courts
2 Bedroom Apartments

Towne Courts

100 Francis Noel WayAnnapolis, MD 21401
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Madison Apartments
2 Bedroom Apartments

Madison Apartments

1000 Madison StAnnapolis, MD 21403
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Americana Southdale
2 Bedroom Apartments

Americana Southdale

7847 Americana CirGlen Burnie, MD 21060
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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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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 The James in the Monticello neighborhood and is 1,314 square feet priced from $3,075. West Woods Apartments has the second largest 2 Bedroom, which is sized at 1,312 square feet and currently listed start at $2,459. Here is today’s list of the largest available 2 Bedroom units in Chester:

Apartment ListingModel NameSquare FootagePriced From
The JamesB2J1,314 Sq Ft$3,075
West Woods ApartmentsThe Marine1,312 Sq Ft$2,459
Stone Point ApartmentsCape Charles (w/loft)1,269 Sq Ft$2,851
Creekstone Village ApartmentsL_CL1,247 Sq Ft$2,596
Obery CourtTwo Bedroom1,204 Sq Ft$1,656
Bay Manor Apartments2 Bedroom1,196 Sq Ft$2,995
Annapolis Bay2 Bedroom, 2 Bathroom 1,177 SF 22C1,177 Sq Ft$2,532
Avalon AnnapolisB1 - Design Collection I - Apt 21211,148 Sq Ft$2,631
MarisB51,139 Sq Ft$3,068
The Promenade at EastonThe Wye1,084 Sq Ft$2,139

Cheapest Available Chester and Nearby 2 Bedroom Apartments

As of August 07, 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+ in the Queen Annes County neighborhood. The second most affordable Chester 2 Bedroom is the B1-2BD/1BA Model at Beacon Pointe Apartments and Townhomes starting at $1,490 in the Evergreen Park Holly Beach neighborhood. The average price for all 2 Bedroom apartments in Chester is currently $2,694. 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$1,490
The Villages at Marley Station ApartmentsB1$1,499
Americana Southdale2 Bedroom Deluxe$1,649
Obery CourtTwo Bedroom$1,656
Nautilus PointNautilus | B1$1,801
Westwinds Apartments2 Bedroom 2 Bath$1,903
Conte Lubrano ApartmentsG$2,095
The Laura House2bd/1ba$2,100
The Promenade at EastonThe Wye$2,139

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

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 $2,694.

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

Today's apartment with the most square footage in Chester is a 1,314 square feet unit starting from $3,075 at The James.

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

The average size for a 2 Bedroom rental in Chester is currently 1,371 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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