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Apartments for Rent in Chester, MD

Average rent

$2,965
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113 Henry Stoupe Way - Photo 1 of 1

4d ago

House for rent in Chester

SINGLE_FAMILY - Colonial - CHESTER, MD

113 Henry Stoupe Way, Chester, MD 21619

In-unit laundry | Garage parking | Swimming pool

3 beds

2 baths

$3,500

House for rent

Elegant Colonial in Vibrant Waterfront Community

A stunning 3-bedroom, 2.5-bath rental home featuring upgrades like a custom stone fireplace, hardwood floors, and granite countertops. Enjoy the fenced backyard with a paver patio and a covered front porch. Community amenities include a pool, clubhouse, and kayak launch, perfect for a blend of comfort and outdoor activities. With 1,844 sq. ft., this Colonial-style home is ready for immediate move-in and offers a welcoming lifestyle!

2626 Cecil Dr - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Colonial - CHESTER, MD

2626 Cecil Dr, Chester, MD 21619

In-unit laundry | Garage parking | Fireplace

3 beds

2 baths

$2,500

House for rent

Charming Colonial Retreat with Spacious Outdoor Area

This delightful 3-bedroom, 2.5-bathroom Colonial home features a bright, open floor plan highlighted by a cozy fireplace. The modern kitchen is equipped with essential appliances, making meal prep a breeze. Enjoy the attached garage and a generous 0.34-acre lot, perfect for outdoor activities. Located just minutes from the Bay Bridge, it offers a peaceful escape while maintaining easy access to Annapolis, Baltimore, and DC. Perfect for those seeking comfort and convenience!

226 Bentons Pleasure Rd - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Contemporary - CHESTER, MD

226 Bentons Pleasure Rd, Chester, MD 21619

In-unit laundry | Garage parking | On-site laundry

4 beds

3 baths

$4,500

House for rent

Waterfront Retreat with Stunning Sunset Views

Experience unparalleled waterfront living in this spacious contemporary home, featuring 4 bedrooms and 3 baths across 2,876 sq. ft. An open-concept kitchen and great room boast a stone fireplace and hardwood floors, while a gourmet kitchen includes granite countertops and stainless steel appliances. Enjoy stunning water views from the master suite or relax on one of three decks. With a private entrance for in-law or office space and pier access, this property is perfect for boaters and sunset lovers alike.

26-C Queen Anne Way - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

Condo - CHESTER, MD

26-C Queen Anne Way, Chester, MD 21619

On-site laundry | Swimming pool | On-site management

2 beds

1 bath

$2,300

Apartment for rent

Charming Penthouse with Community Amenities Galore

This inviting 2-bedroom, 1.5-bath penthouse features Mediterranean architecture and a spacious layout. Enjoy in-unit laundry hookups, a refreshing outdoor pool, and access to a fitness room and tennis courts. With well-maintained common areas and on-street parking, this lovely apartment in the serene Queens Landing community offers the perfect balance of comfort and convenience for a vibrant lifestyle.

2605 Harrington Rd - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Ranch - CHESTER, MD

2605 Harrington Rd, Chester, MD 21619

In-unit laundry | Hardwood floor | Walk-in closets

4 beds

2 baths

$2,950

House for rent

Spacious Ranch Home with Fenced Backyard Retreat

This beautiful 4-bedroom ranch-style home features a bright and open kitchen with stainless steel appliances and granite countertops. Hardwood floors flow throughout the spacious layout. Energy efficiency upgrades include an insulated crawlspace and R49 attic insulation. Enjoy the serene, fenced backyard on a quiet street. Perfect for families or those seeking extra space to unwind. Available starting June 1, 2026, with rental applications available online.

907 Auckland Way - Photo 1 of 1

5d+ ago

Townhouse for rent in Chester

Condo - CHESTER, MD

907 Auckland Way, Chester, MD 21619

In-unit laundry | Furnished | Garage parking

3 beds

3 baths

$3,200

House for rent

Waterfront Townhouse with Stunning Chesapeake Views

Rare end-unit townhouse offering over 2,100 sq ft of elegant living in a sought-after waterfront community. This beautifully renovated 3-bedroom, 3.5-bath home features a modern kitchen with quartz countertops, a gas fireplace, and breathtaking river views from all three levels. Enjoy private decks, a community pool, tennis courts, and nearby marina access. Perfect for those looking for resort-style living with easy access to Annapolis, DC, and Baltimore, plus included lawn care and maintenance.

2201 Main St #101 - Photo 1 of 1

5d+ ago

Condo for rent in Chester

Chester Centre Apartments

2201 Main St #101, Chester, MD 21619

In-unit laundry | On-site laundry | Central heat

2 beds

1 bath

$1,950

Condo for rent

Available Mar 1

Spacious Townhome with Secure Entry & Modern Style

This charming 2-bedroom, 1.5-bath townhome-style apartment spans approximately 1,200 square feet, featuring large rooms and in-unit laundry for convenience. Located in the Chester Centre building with secured entry, this property offers a desirable living space available in early October. Perfect for those seeking comfort and a pet-friendly environment in a fantastic location.

170 Harrier Way - Photo 1 of 1
Age restricted

5d+ ago

Condo for rent in Chester

Condo - CHESTER, MD

170 Harrier Way, Chester, MD 21619

In-unit laundry | Garage parking | On-site laundry

2 beds

2 baths

$3,700

Condo for rent

Luxurious Main Level Condo with Scenic Views

This stunning main-level condo offers 2,000 sq. ft. of luxurious living in a vibrant 55+ community! Features include a gourmet kitchen, spacious family room with an electric fireplace, and a private primary wing complete with an ensuite bath. Enjoy easy access with no stairs, a lovely patio, and a 1-car garage. Residents will appreciate the rich amenities, including a clubhouse, indoor pool, and sports facilities, all while being surrounded by beautiful nature trails.

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721 Main St #204 - Photo 1 of 1

5d+ ago

Apartment for rent in Stevensville

721 Main St #204, Stevensville, MD 21666

In-unit laundry | Dishwasher | Microwave

2 beds

1 bath

$1,850

Apartment for rent

Available Apr 1

215 Keenan Way - Photo 1 of 1

5d+ ago

Townhouse for rent in Stevensville

Condo - STEVENSVILLE, MD

215 Keenan Way, Stevensville, MD 21666

In-unit laundry | Garage parking | On-site laundry

3 beds

3 baths

$2,990

House for rent

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Swimming Pool

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120 Anthony Ln - Photo 1 of 1

5d+ ago

Townhouse for rent in Stevensville

TOWNHOME - Contemporary, Colonial - STEVENSVILLE, MD

120 Anthony Ln, Stevensville, MD 21666

In-unit laundry | Garage parking | Swimming pool

3 beds

2 baths

$2,975

House for rent

235 Jessica Lyn Ave - Photo 1 of 1
New construction

5d+ ago

Townhouse for rent in Stevensville

235 Jessica Lyn Ave

235 Jessica Lyn Ave, Stevensville, MD 21666

In-unit laundry | Garage parking | On-site laundry

4 beds

3 baths

$3,500

House for rent

Available Apr 15

714 Old Love Point Rd - Photo 1 of 1
3D tour

5d+ ago

House for rent in Stevensville

714 old love point road

714 Old Love Point Rd, Stevensville, MD 21666

In-unit laundry | Air conditioning | Garage parking

4 beds

2 baths

$3,295

House for rent

Available Feb 14

Bay Manor- Residential - Photo 1 of 1

12h ago

8.6

Very good

Bay Manor- Residential

214 Pier 1 Rd, Stevensville, MD 21666

In-unit laundry | Air conditioning | Balcony

Studio–2 beds

1–2 baths

$1,950–$3,450

Condo for rent

108 S Carolina Rd - Photo 1 of 1

5d+ ago

House for rent in Stevensville

SINGLE_FAMILY - Rambler - STEVENSVILLE, MD

108 S Carolina Rd, Stevensville, MD 21666

Garage parking | Ceiling fan | Storage

3 beds

2 baths

$3,000

$2,900

Price drop

House for rent

2620 Love Point Rd - Photo 1 of 1

5d+ ago

House for rent in Stevensville

SINGLE_FAMILY - STEVENSVILLE, MD

2620 Love Point Rd, Stevensville, MD 21666

In-unit laundry | Furnished | Ceiling fan

5 beds

5 baths

$5,500

House for rent

Find sweet deals near Chester

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

216 Perrys Retreat Blvd - Photo 1 of 1

5d+ ago

House for rent in Grasonville

SINGLE_FAMILY - Other - GRASONVILLE, MD

216 Perrys Retreat Blvd, Grasonville, MD 21638

Garage parking | Walk-in closets | Package service

5 beds

3 baths

$3,500

$3,300

Price drop

House for rent

Obery Court - Photo 1 of 1
Income restricted

5h 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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980 Breakwater Dr #NA - Photo 1 of 1

1h ago

Our team has verified this company

Verified

$2950 - 3 Bedroom 2.5 Bathroom House In Annapolis - 9 min from Naval Academy

980 Breakwater Dr #NA, Annapolis, MD 21403

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

3 beds

2 baths

$2,900

House for rent

Available Mar 1

126 Tred Avon Ave #NA - Photo 1 of 1

2d ago

Our team has verified this company

Verified

Single family home for lease / Tred Avon Ave. Easton, Maryland, 21601 - Premiere Property listing

126 Tred Avon Ave #NA, Easton, MD 21601

In-unit laundry | Air conditioning | Garage parking

4 beds

2 baths

$3,000

House for rent

Available May 1

8478 Garden Rd - Photo 1 of 1
New construction
3D tour

1h ago

Our team has verified this company

Verified

8478 Garden Rd, Riviera Beach, MD 21122

Garage parking | On-site laundry | Ceiling fan

4 beds

2 baths

$3,825

$3,325

Price drop

House for rent

Available Jan 23

5 Dean Street - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

5 Dean Street, Annapolis, MD 21401

In-unit laundry | Air conditioning | Balcony

3 beds

2 baths

$4,500

House for rent

Available Mar 1

768B Fairview Ave Unit 768 - Photo 1 of 1

21h ago

Condo for rent in Annapolis

768B Fairview Ave Unit 768, Annapolis, MD 21403

Walk-in closets | Outdoor space

3 beds

2 baths

$4,000

Condo for rent

1576 Bay Head Rd - Photo 1 of 1

3d ago

House for rent in Annapolis

SINGLE_FAMILY - Craftsman, Colonial - ANNAPOLIS, MD

1576 Bay Head Rd, Annapolis, MD 21409

In-unit laundry | Garage parking | On-site laundry

6 beds

5 baths

$14,000

House for rent

150 Spa Dr - Photo 1 of 1

4d ago

House for rent in Annapolis

SINGLE_FAMILY - Contemporary - ANNAPOLIS, MD

150 Spa Dr, Annapolis, MD 21403

In-unit laundry | Garage parking | Balcony

3 beds

2 baths

$3,900

House for rent

Showing 1 - 25 of 25 results
Home > Apartments in Chester
Updated: March 17, 2026

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Learn more about renting in Chester, MD

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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.

Chester, MD apartment availability

Chester's rental market is relatively small, with an average of 12 listings available per month. The most common apartment sizes are 2-bedroom units, accounting for 33% of the total market, followed closely by 1-bedroom and 3-bedroom units, each making up 25% of the market. Studios are also available, but less common. Many Chester apartments offer convenient amenities, with air conditioning being a common feature, available in 75% of listings. In-unit laundry is also widely available, found in 67% of apartments, and a dishwasher is a feature in 58% of listings. These figures are based on historical data, but they should give you a sense of what to expect in the current market. Renters in Chester will need to be prepared to act quickly when a suitable apartment becomes available.

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 2024 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.

Apartment rentals Chester, MD FAQ

What is the average size of an apartment in Chester, MD?

The average size of a 2 bedroom apartment rental in Chester is 959 square feet. The average size of a 3 bedroom apartment rental in Chester is 1102 square feet.

Can I afford an apartment for rent in Chester, MD?

To help you better understand how much rent you can afford, check out Zumper's rent calculator. Our rent calculator can help you learn more about Chester average rent prices.

Looking for apartments in Chester, MD near you?

🔑Available apartment rentals25
💰Best rent deal199 Bertina A Nick Way
Popular amenities, ,
🍽With dishwasher
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