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

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property at 4000 Herons Nest Wy
$4,200

Total Monthly Price

Base Rent$4,200
Total Monthly Price$4,200
2 Bedroom, 3 Bath Condo for Rent
Available Now
Furnished

4000 Herons Nest Wy, Unit 42

4000 Herons Nest Wy
ChesterMD21619

Exploring Rental Options: Apartments, Townhomes, and Lofts—Oh My!

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Maris
Rent Specials
$2,764 - $3,037

Total Monthly Price

Base Rent$1,907 - $4,766
Total Monthly PriceVaries
2 Bedroom Apartments Available Now

Maris

2445 Holly AveAnnapolis, MD 21401
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Aventon Annapolis
Rent Specials
$2,854 - $3,481

Total Monthly Price

Base Rent$2,055 - $4,960
Total Monthly PriceVaries
2 Bedroom Apartments Available Now

Aventon Annapolis

2553 Riva RdAnnapolis, MD 21401
Luxury
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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Looking for the perfect new rental? Learn great ways to spot the perfect apartment for you, identify common red flags, and avoid rental issues and scams with these expert provided actionable tips.

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Bayshore Landing
$1,893 - $2,073

Total Monthly Price

Base Rent$1,860 - $2,110
Total Monthly Price$1,860 - $2,110
2 Bedroom Apartments Available Sep 30

Bayshore Landing

988 Spa RdAnnapolis, MD 21403
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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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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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Mulberry Estates
2 Bedroom Apartments

Mulberry Estates

1020-1070 N Washington StEaston, MD 21601
  • Utilities Included

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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Chester, MD Local Guide

Largest Available Chester 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Chester, MD is found at Spa Cove Apartments in the Annapolis neighborhood and is 1,872 square feet priced from $2,300. West Woods Apartments in the Monticello neighborhood has the second largest 2 Bedroom, which is sized at 1,312 square feet and currently listed start at $2,437. Here is today’s list of the largest available 2 Bedroom units in Chester:

Apartment ListingModel NameSquare FootagePriced From
Spa Cove ApartmentsChester1,872 Sq Ft$2,300
West Woods ApartmentsThe Marine1,312 Sq Ft$2,437
Creekstone Village ApartmentsM_CL1,263 Sq Ft$2,375
Bell Annapolis on WestB2G1,251 Sq Ft$2,450
Aventon AnnapolisB7 Den1,222 Sq Ft$3,425
Obery CourtTwo Bedroom1,204 Sq Ft$1,656
Annapolis Bay2 Bedroom, 2 Bathroom 1,177 SF 22C1,177 Sq Ft$2,502
MarisB6.11,146 Sq Ft$2,771
Stone Point ApartmentsPoint Lookout1,110 Sq Ft$2,406
Conte Lubrano ApartmentsG1,099 Sq Ft$2,095

Cheapest Available Chester 2 Bedroom Apartments

As of September 22, 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 Nautilus | B1 Model at Nautilus Point starting at $1,607 in the Highland Beach neighborhood. The average price for all 2 Bedroom apartments in Chester is currently $2,748. 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
Nautilus PointNautilus | B1$1,607
Americana Southdale2 Bedroom$1,639
Obery CourtTwo Bedroom$1,656
The Villages at Marley Station ApartmentsB2$1,663
Beacon Pointe Apartments and TownhomesB2 - 2BD/1BA with Den$1,675
Harbour Gates Apartments2 Bedrooms + 1 Bath$1,958
Spa Cove ApartmentsChesapeake$2,002
Conte Lubrano ApartmentsG$2,095
Annapolis Roads Apartments2BR 2BA$2,128

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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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 $2,748.

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

Today's apartment with the most square footage in Chester is a 1,872 square feet unit starting from $2,300 at Spa Cove 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 1,900 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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Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

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Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.