20 Windwhisper Ln
AnnapolisMD21403
Cheap Homes for Rent in Chester, MD from $900 (11 Rentals)
Search the lowest-cost Homes available for rent right now in Chester.
101 Charles St
AnnapolisMD21401
111 Academy St
AnnapolisMD21401
776 Southern Hills Dr
ArnoldMD21012
203 Victor Pkwy
AnnapolisMD21403
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
235 Bryce Rd
QueenstownMD21658
2014 Gov Thomas Baden Way
AnnapolisMD21401
1127 Lake Heron Dr
AnnapolisMD21403
24345 Widgeon Pl
Saint MichaelsMD21663
645 Oakland Hills Dr
ArnoldMD21012
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.
25 Dorchester Ct
AnnapolisMD21403
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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 | $2,468 | $2,000 | $3,000 |
| Chester 3 Bedroom Homes for Rent | $3,141 | $2,150 | $4,500 |
| Chester 4 Bedroom Homes for Rent | $4,452 | $3,195 | $6,700 |
| Chester 5 Bedroom Homes for Rent | $4,250 | $3,500 | $5,000 |
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Chester, MD Local Guide
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Cheapest Available Chester Apartments for Rent and Nearby
The cheapest available apartment rental in Chester, MD is a 2 Beds unit found at Mulberry Estates in the Chesapeake by Del Webb neighborhood priced from $1,054. The Villages at Marley Station Apartments in the Sloop Cove Landing neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,091. Here is today’s list of the most affordable Chester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Mulberry Estates | two bedroom | 2BR,1BA | $1,054 |
| The Villages at Marley Station Apartments | S1 | Studio,1BA | $1,091 |
| Obery Court | Two Bedroom | 2BR,1BA | $1,229 |
| The Village at Slippery Hill Senior Apartments | B1 - Two Bedroom | 2BR,1BA | $1,265 |
| Beacon Pointe Apartments and Townhomes | A1-1BD/1BA | 1BR,1BA | $1,317 |
Best Value Apartments for Rent in Chester, MD and Nearby
As of November 13, 2025 the best value apartment in the Chester area is the $1.11 price per square foot Three Bedroon Model at Obery Court in the in the Monticello neighborhood starting from $1,415. The second greatest value Chester apartment is the 2 Bedroom, 1.5 Bathroom - Accessible (Flat) Model at Towne Courts starting at $1,382 with a $1.26 price per square foot in the Monticello 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. |
|---|---|---|---|
| Obery Court | Three Bedroon | 3BR,2BA | $1.11 |
| Towne Courts | 2 Bedroom, 1.5 Bathroom - Accessible (Flat) | 2BR,1.5BA | $1.26 |
| The Reserve at Stoney Creek | The Sloop | 2BR,2BA | $2.12 |
| Spa Cove Apartments | West | 2BR,2BA | $2.14 |
| The Village at Slippery Hill Senior Apartments | B1 - Two Bedroom | 2BR,1BA | $1.48 |
| Mulberry Estates | two bedroom | 2BR,1BA | $1.26 |
| Annapolis Roads | 1BR 1BA | 1BR,1BA | $1.99 |
| Harbour Gates Apartments | 1 Bedroom + 1 Bath | 1BR,1BA | $1.93 |
| The Promenade at Easton | The Chester | 1BR,1BA | $2.10 |
| Conte Lubrano Apartments | L | 1BR,1BA | $2.16 |
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.
Read Article
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 ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleQuick Rent Budget Calculator
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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 53 Apartments for Rent in Chester, MD with pricing that ranges from $981 to $4,119. There are also 37 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $940 to $6,700.
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 $940 to $6,700 with an average monthly rent of $3,131.
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 $1,415 to $4,030, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,150 to $4,500. Four Bedroom Single-Family rentals are also available starting from $3,195 and Four Bedroom Apartments start at $2,995.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.