20 Windwhisper Ln
AnnapolisMD21403
Cheap Homes for Rent in Chester, MD from $1,000 (13 Rentals)
Search the lowest-cost Homes available for rent right now in Chester.
7826 Bodkin View Dr
PasadenaMD21122
111 Academy St
AnnapolisMD21401
15 N Brewer Ave
AnnapolisMD21401
7828 Bodkin View Dr
PasadenaMD21122
5 Murray Ave
AnnapolisMD21401
1424 Greendale Ct
ArnoldMD21012
10 Hearthstone Ct
AnnapolisMD21403
611 Oakland Hills Ct
ArnoldMD21012
5810 Clam Cove
Rock HallMD21661
1138 Cove Rd
AnnapolisMD21403
50j Sandstone Ct
AnnapolisMD21403
1134 Cove Rd
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 | $2,207 | $1,600 | $3,200 |
| Chester 3 Bedroom Homes for Rent | $3,020 | $2,000 | $5,000 |
| Chester 4 Bedroom Homes for Rent | $4,104 | $3,395 | $6,700 |
| Chester 5 Bedroom Homes for Rent | $6,000 | $5,000 | $7,000 |
| Chester 6 Bedroom Homes for Rent | $3,600 | $3,600 | $3,600 |
Browse Top Homes for Rent in Chester
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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 The Village at Slippery Hill II priced from $699. Mulberry Estates in the Chesapeake by Del Webb neighborhood has the second lowest priced unit, which is a 2 Beds apartment currently listed from $1,054. 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 II | B1 - Two Bedroom Townhome | 2BR,1BA | $699 |
| Mulberry Estates | two bedroom | 2BR,1BA | $1,054 |
| The Villages at Marley Station Apartments | A2 | 1BR,1BA | $1,247 |
| Beacon Pointe Apartments and Townhomes | A1-1BD/1BA | 1BR,1BA | $1,317 |
| Towne Courts | 2 Bedroom, 1.5 Bathroom - Accessible (Flat) | 2BR,1BA | $1,382 |
Best Value Apartments for Rent in Chester, MD and Nearby
As of September 14, 2025 the best value apartment in the Chester area is the $1.60 price per square foot F Model at Conte Lubrano Apartments in the in the Monticello neighborhood starting from $2,025. The second greatest value Chester apartment is the Two Bedroom Model at Obery Court starting at $1,943 with a $1.61 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. |
|---|---|---|---|
| Conte Lubrano Apartments | F | 2BR,2BA | $1.60 |
| Obery Court | Two Bedroom | 2BR,1.5BA | $1.61 |
| Towne Courts | 2 Bedroom, 1.5 Bathroom - Accessible (Flat) | 2BR,1.5BA | $1.26 |
| The Reserve at Stoney Creek | The Clipper | 2BR,2BA | $2.17 |
| The Village at Slippery Hill II | B3 - Two Bedroom Townhome | 2BR,1.5BA | $1.02 |
| Mulberry Estates | two bedroom | 2BR,1BA | $1.26 |
| Spa Cove Apartments | Severn | 1BR,1BA | $2.30 |
| Annapolis Roads | 1BR 1BA | 1BR,1BA | $2.15 |
| Harbour Gates Apartments | 1 Bedroom + 1 Bath | 1BR,1BA | $2.19 |
| Beacon Pointe Apartments and Townhomes | A1-1BD/1BA | 1BR,1BA | $2.20 |
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Frequently Asked Questions about Chester
What type of rentals are currently available in Chester?
There are currently 50 Apartments for Rent in Chester, MD with pricing that ranges from $666 to $4,412. There are also 46 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,050 to $23,000.
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 $1,050 to $23,000 with an average monthly rent of $6,232.
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 $1,675 to $4,412, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,000 to $5,000. Four Bedroom Single-Family rentals are also available starting from $3,395 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.
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.
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.