41A Queen Catherine Ct
ChesterMD21619
Cheap Homes for Rent in Chester, MD from $1,400 (11 Rentals)
Search the lowest-cost Homes available for rent right now in Chester.
1712 Main St
ChesterMD21619
173 Browns Woods Rd
AnnapolisMD21409
600 Perrys Corner Rd
GrasonvilleMD21638
2201 Main St
ChesterMD21619
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
645 Oakland Hills Dr
ArnoldMD21012
145 King George St
AnnapolisMD21401
13 Mariners Way
StevensvilleMD21666
6808 Main St
QueenstownMD21658
93 Great Lake Dr
AnnapolisMD21403
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.
147 King George St
AnnapolisMD21401
Showing Results 1-11, Page 1 of 1
Chester, MD Local Guide
Smith Island Cake by Jane Thomas is licensed under CC BY 2.0
How much does it cost to rent a home in Chester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chester 2 Bedroom Homes for Rent | $2,520 | $1,400 | $3,295 |
| Chester 3 Bedroom Homes for Rent | $3,370 | $1,595 | $7,500 |
| Chester 4 Bedroom Homes for Rent | $4,238 | $2,750 | $9,500 |
| Chester 5 Bedroom Homes for Rent | $3,800 | $3,800 | $3,800 |
| Chester 6 Bedroom Homes for Rent | $6,200 | $6,200 | $6,200 |
Browse Top Homes for Rent in Chester
Explore Chester
Chester, MD Local Guide
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Chester Apartments for Rent and Nearby
The cheapest available apartment rental in Chester, MD is a 1 Bed unit found at The Village at Slippery Hill Senior Apartments- 62+ in the Queen Annes County neighborhood priced from $1,080. The Villages at Marley Station Apartments in the Sloop Cove Landing neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,264. Here is today’s list of the most affordable Chester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Village at Slippery Hill Senior Apartments- 62+ | A5 - One Bedroom | 1BR,1BA | $1,080 |
| The Villages at Marley Station Apartments | A2 | 1BR,1BA | $1,264 |
| Beacon Pointe Apartments and Townhomes | A1-1BD/1BA | 1BR,1BA | $1,317 |
| Chatham Village Apartments | I Bedroom Delux | 1BR,1BA | $1,330 |
| Obery Court | One Bedroom | 1BR,1BA | $1,389 |
Best Value Apartments for Rent in Chester, MD and Nearby
As of August 08, 2026 the best value apartment in the Chester area is the $2.05 price per square foot The Schooner Model at The Reserve at Stoney Creek in the in the Pasadena neighborhood starting from $2,770. The second greatest value Chester apartment is the The Miles Model at The Promenade at Easton starting at $2,445 with a $1.98 price per square foot in the Chesapeake by Del Webb neighborhood. Here is today’s list of the best values for Chester apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| The Reserve at Stoney Creek | The Schooner | 3BR,2BA | $2.05 |
| The Promenade at Easton | The Miles | 3BR,2BA | $1.98 |
| West Woods Apartments | The Chester | 2BR,2BA | $1.95 |
| Conte Lubrano Apartments | G | 2BR,2BA | $1.91 |
| The Laura House | 2bd/1ba | 2BR,1BA | $1.94 |
| 102 B Marlboro Ave | 1 Bedroom | 1BR,1BA | $1.84 |
| Obery Court | One Bedroom | 1BR,1BA | $1.79 |
| Quiet Waters Landing | A2-1BD/1BA | 1BR,1BA | $2.03 |
| Chatham Village Apartments | I Bedroom Delux | 1BR,1BA | $2.05 |
| The Village at Slippery Hill Senior Apartments- 62+ | A5 - One Bedroom | 1BR,1BA | $1.69 |
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.
Read Article
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.
Read Article
Quick Rent Budget Calculator
How much rent can you afford?
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.
Let everyone know!
Do you know the Chester area?
If you’re an expert on all things Chester, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Chester, MD Rentals by Map
See the most popular apartments and homes in Chester, MD
Frequently Asked Questions about Chester
What type of rentals are currently available in Chester?
There are currently 52 Apartments for Rent in Chester, MD with pricing that ranges from $1,252 to $6,482. There are also 46 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,400 to $9,500.
What is the current price range for Rental Homes in Chester?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Chester ranges from $1,400 to $9,500 with an average monthly rent of $3,393.
How much are larger Three and Four Bedroom Rentals in Chester?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Chester range from $1,915 to $6,482, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,595 to $7,500. Four Bedroom Single-Family rentals are also available starting from $2,750 and Four Bedroom Apartments start at $2,995.
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
Rent According to Income: A Look at Income-Restricted Rentals
Written by: Robin Stewart
The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
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.
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.
Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.