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Apartments for Rent in Chester, MD

Average rent

$2,500
decreased by11%

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114 Golden Eye Ct - Photo 1 of 1

3d ago

Condo for rent in Chester

114 Golden Eye Ct, Chester, MD 21619

In-unit laundry | Air conditioning | On-site laundry

2 beds

2 baths

$2,100

Condo for rent

2-bed waterfront condo with pool and gym access

Set in Chester, MD, this 2-bed, 2-bath second-floor condo offers water views and updated kitchen and bathrooms. The 1,062 sqft layout includes in-unit laundry, dedicated parking, and a smart thermostat. Community amenities feature a pool and fitness center, with commuter access just 5 minutes from the Bay Bridge and 2 minutes from Route 50 to Annapolis and Baltimore.

6002 Bridgepointe Dr - Photo 1 of 1

3d ago

Townhouse for rent in Chester

TOWNHOME - CHESTER, MD

6002 Bridgepointe Dr, Chester, MD 21619

3 beds

2.5 baths

$2,500

House for rent

3-bed townhouse near Rt 50 with heat pump

Townhouse in Chester, MD, this spacious 3-bed, 2.5-bath unit spans two floors with central air and heat pump heating. The 1,586 sqft layout sits in Bridge Pointe Townhouse subdivision with convenient access to Route 50. Brick and combination exterior adds curb appeal, with pets considered case by case.

230 Switchgrass Way #21 - Photo 1 of 1
Age restricted
New construction

5d+ ago

Condo for rent in Chester

CONDOS - Other - CHESTER, MD

230 Switchgrass Way #21, Chester, MD 21619

Garage parking | On-site laundry | Balcony

3 beds

2.5 baths

$4,300

Condo for rent

3-bed waterfront condo with resort amenities

Quietly set in Chester, MD, this 3-bed, 2.5-bath end-unit condo offers 2,602 sqft in a 55+ waterfront community along the Chester River. The Severn model features a gourmet kitchen with quartz countertops, GE Profile appliances, and an oversized island flowing to a corner balcony. Residents enjoy a 24,000 sqft clubhouse with pools, fitness center, tennis courts, and walking trails.

400 Schooner Way - Photo 1 of 1

5d+ ago

Townhouse for rent in Chester

Townhouse, End of Row/Townhouse - CHESTER, MD

400 Schooner Way, Chester, MD 21619

In-unit laundry | Garage parking | Swimming pool

3 beds

2.5 baths

$2,600

House for rent

3-level townhouse with garage and pool access

Right in Chester, MD, this 3-bed, 2.5-bath townhouse spans three levels with garage parking and pond views. In-unit laundry, dishwasher, and central air complement community amenities including a swimming pool, tennis courts, and exercise room. Close to Route 50 for easy commuting access and walkable to local restaurants.

2006 Stevens Dr - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Rambler - CHESTER, MD

2006 Stevens Dr, Chester, MD 21619

In-unit laundry | Hardwood floor | Outdoor space

3 beds

1.5 baths

$2,500

House for rent

Renovated 3-bed rambler near Bay Bridge

Set in Chester, MD, this fully renovated 3-bed, 1.5-bath rambler sits minutes from the Bay Bridge with easy Route 50 access. The 1,120 sqft layout features a new kitchen, updated bathrooms, hardwood floors, and central air throughout an open, light-filled interior. A covered front porch and partially fenced backyard add outdoor space, while in-unit laundry completes the package.

812 Petinot Pl - Photo 1 of 1

2d ago

House for rent in Stevensville

Detached, Single Family - STEVENSVILLE, MD

812 Petinot Pl, Stevensville, MD 21666

Garage parking | Swimming pool | Ceiling fan

3 beds

2 baths

$2,795

House for rent

3809 Main St - Photo 1 of 1

5d+ ago

House for rent in Grasonville

SINGLE_FAMILY - National - GRASONVILLE, MD

3809 Main St, Grasonville, MD 21638

On-site laundry | Storage | Dishwasher

2 beds

2 baths

$2,800

House for rent

341 Creekside Commons Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Stevensville

TOWNHOME - Other - STEVENSVILLE, MD

341 Creekside Commons Ct, Stevensville, MD 21666

In-unit laundry | Ceiling fan | Dishwasher

2 beds

2.5 baths

$2,550

House for rent

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Bay Manor- Residential - Photo 1 of 1

15h ago

8.5

Very good

Bay Manor- Residential

214 Pier 1 Rd, Stevensville, MD 21666

In-unit laundry | Air conditioning | Balcony

Studio–1 bed

1 bath

$2,000–$2,600

Condo for rent

117 Rebel Rd - Photo 1 of 1

4d ago

House for rent in Grasonville

SINGLE_FAMILY - Ranch - GRASONVILLE, MD

117 Rebel Rd, Grasonville, MD 21638

In-unit laundry | On-site laundry | Ceiling fan

3 beds

2 baths

$2,850

House for rent

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4819 Main St - Photo 1 of 1

5d+ ago

Townhouse for rent in Grasonville

TOWNHOME - National - GRASONVILLE, MD

4819 Main St, Grasonville, MD 21638

Garage parking | Walk-in closets

3 beds

2.5 baths

$2,300

House for rent

1006 Bayside Dr - Photo 1 of 1

5d+ ago

House for rent in Stevensville

1006 Bayside Dr, Stevensville, MD 21666

In-unit laundry | Dishwasher | Oven

3 beds

4 baths

$6,500

$6,000

Price drop

House for rent

Listings within 10 miles
215 Thompson Ave - Photo 1 of 1

4d ago

Townhouse for rent in Queenstown

215 Thompson Ave

215 Thompson Ave, Queenstown, MD 21658

In-unit laundry | Air conditioning | Garage parking

3 beds

2.5 baths

$2,600

House for rent

Available Aug 15

301 Wicomico Rd - Photo 1 of 1

5d+ ago

House for rent in Stevensville

SINGLE_FAMILY - Other - STEVENSVILLE, MD

301 Wicomico Rd, Stevensville, MD 21666

In-unit laundry | Hardwood floor | Ceiling fan

3 beds

1 bath

$2,400

House for rent

108 Wilson Rd - Photo 1 of 1

5d+ ago

House for rent in Grasonville

SINGLE_FAMILY - Ranch - GRASONVILLE, MD

108 Wilson Rd, Grasonville, MD 21638

In-unit laundry | Furnished | Dishwasher

3 beds

2 baths

$3,000

House for rent

Find sweet deals near Chester

These rentals are 10%-30% cheaper than the local average price for similar rentals.

132APARTME Greenwood Creek Rd - Photo 1 of 1

5d+ ago

Apartment for rent in Queenstown

SINGLE_FAMILY - QUEENSTOWN, MD

132APARTME Greenwood Creek Rd, Queenstown, MD 21658

In-unit laundry | Garage parking | Assigned parking

1 bed

1 bath

$2,000

Apartment for rent

104 New Jersey Rd #NA - Photo 1 of 1

5d+ ago

House for rent in Stevensville

Live the Kent Island lifestyle without paying Annapolis prices.

104 New Jersey Rd #NA, Stevensville, MD 21666

In-unit laundry | Air conditioning | Garage parking

3 beds

2.5 baths

$3,600

House for rent

Available Jun 1

105 King George Ct - Photo 1 of 1

5d+ ago

House for rent in Stevensville

SINGLE_FAMILY - Rambler - STEVENSVILLE, MD

105 King George Ct, Stevensville, MD 21666

Garage parking | Hardwood floor | Walk-in closets

4 beds

3 baths

$4,400

House for rent

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Obery Court - Photo 1 of 1
Income restricted

10m ago

9.2

Excellent

Our team has verified this company

Verified

Obery Court

199 Bertina A Nick Way, Annapolis, MD 21401

On-site management | Residents lounge

1–3 beds

1–2 baths

$1,046–$1,444

Apartment for rent

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910 Windsor Ave - Photo 1 of 1

2h ago

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Verified

910 Windsor Ave, Annapolis, MD 21403

In-unit laundry | Furnished | Air conditioning

3 beds

2 baths

$8,044

$7,687

Price drop

Apartment for rent

111 Clay St - Photo 1 of 1

2h ago

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Verified

111 Clay St, Annapolis, MD 21401

In-unit laundry | Furnished | Air conditioning

3 beds

1.5 baths

$7,145

Apartment for rent

2078 Forest Dr - Photo 1 of 1

4d ago

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Verified

2078 Forest Dr, Annapolis, MD 21401

In-unit laundry | Furnished | Air conditioning

2 beds

2 baths

$5,278

Apartment for rent

Wiley Bates - Photo 1 of 1
Age restricted
Rent special

5d+ ago

9.9

Excellent

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Wiley Bates

1103 Smithville St, Annapolis, MD 21401

On-site laundry | Ceiling fan | Carpet

1 bed

1 bath

$1,993

Apartment for rent

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College Parkway Place - Photo 1 of 1
Rent special

5d+ ago

9.9

Excellent

Our team has verified this company

Verified

College Parkway Place

570 Bellerive Rd, Cape St. Claire, MD 21409

Air conditioning | On-site laundry | Balcony

1 bed

1 bath

$1,950

Apartment for rent

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Admiral Oaks - Photo 1 of 1

4d ago

9.3

Excellent

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Verified

Admiral Oaks

445 Captains Cir Ste C, Annapolis, MD 21401

Air conditioning | On-site laundry | Hardwood floor

2–3 beds

1 bath

$1,453–$1,534

Apartment for rent

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Showing 1 - 25 of 25 results
Home > Apartments in Chester
Updated: June 16, 2026

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Learn more about renting in Chester, MD

Local insights: What it's like to live in Chester, MD

In Chester, MD, residents appreciate the quiet, suburban atmosphere and the proximity to waterfront activities, which makes outdoor enjoyment a significant part of daily life. Many highlight the convenient access to shopping, dining, and parks, creating a manageable and pleasant environment for families. However, some locals mention that public transportation options are limited, making a car necessary for commuting and errands. Overall, the area offers a laid-back lifestyle with a mix of local amenities, though it may not suit those seeking a more bustling urban experience.

Are utilities usually included in rent in Chester, MD?

Chester apartments rarely include utilities as part of the rent package. Less than 1% of total listings across all bedroom types include utilities in their rental rates.

Are most apartments in Chester, MD largely older buildings or new developments?

Chester's rental market features a mix of architectural styles, with contemporary design representing the most common style at 29% of available properties. Contemporary architecture emphasizes clean lines, open floor plans, and large windows that prioritize natural light and flexible living spaces.

Methodology: How we got this data

Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2026 rental inventory and prices.

Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.

Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.

Looking for apartments in Chester, MD near you?

🔑Available apartment rentals25
💰Best rent deal214 Pier 1 Rd
Popular amenities, ,
🍽With dishwasher
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