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Houses for Rent in Chester, MD

Average rent

$3,100

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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 | Outdoor space | Garage parking

3 beds

2.5 baths

$2,600

House for rent

Charming Bayside Townhome with Pool Access

Embrace the island lifestyle in this delightful 3-level townhouse featuring 2-3 bedrooms and garage parking. Enjoy serene pond views and a community pool, along with tennis courts and an exercise room. Conveniently located near Route 50 and within walking distance to restaurants, this home offers comfort and convenience for an active lifestyle. Ideal for those seeking community amenities and a vibrant living experience.

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 | Outdoor space | Hardwood floor

3 beds

1.5 baths

$2,500

House for rent

Brightly Renovated Ranch Near Bay Bridge Excitement

This fully renovated 3-bedroom, 1.5-bath ranch home offers a fresh, modern vibe with an airy layout and abundant natural light. Key features include a new kitchen with updated appliances, stylish flooring, and a charming covered porch. The partially fenced backyard is perfect for outdoor entertaining. Conveniently located near Route 50 and the Bay Bridge, this home provides easy access to parks, restaurants, shopping, and waterfront fun. Enjoy coastal living at its finest!

2605 Harrington Rd - Photo 1 of 1

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Rambler - CHESTER, MD

2605 Harrington Rd, Chester, MD 21619

In-unit laundry | Outdoor space | Hardwood floor

4 beds

2.5 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.

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 | Outdoor space | Storage

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 | Outdoor space | Ceiling fan

2 beds

2.5 baths

$2,550

House for rent

307 Irene Way - Photo 1 of 1

5d+ ago

House for rent in Stevensville

Kent Island Waterfront Home for Rent

307 Irene Way, Stevensville, MD 21666

In-unit laundry | Outdoor space | Storage

3 beds

1 bath

$2,750

House for rent

Available Apr 27

Nearby rental good for eco-living

Nearby rental good for pet owners

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

107 Winchester Ave #107 - Photo 1 of 1

5d+ ago

House for rent in Grasonville

SINGLE_FAMILY - Ranch, Cottage - GRASONVILLE, MD

107 Winchester Ave #107, Grasonville, MD 21638

In-unit laundry | Outdoor space | Air conditioning

1 bed

1 bath

$1,800

House for rent

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Listings within 10 miles
301 Wicomico Rd - Photo 1 of 1

16h ago

House for rent in Stevensville

301 Wicomico Rd, Stevensville, MD 21666

In-unit laundry | Outdoor space | Carpet

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 - Rambler - GRASONVILLE, MD

108 Wilson Rd, Grasonville, MD 21638

In-unit laundry | Furnished | Dishwasher

3 beds

2 baths

$3,000

House 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 | Outdoor space | Garage parking

3 beds

2.5 baths

$3,600

House for rent

Available Jun 1

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

105 King George Ct - Photo 1 of 1

4d ago

House for rent in Stevensville

SINGLE_FAMILY - Rambler - STEVENSVILLE, MD

105 King George Ct, Stevensville, MD 21666

Outdoor space | Garage parking | Hardwood floor

4 beds

3 baths

$4,400

House for rent

Listings within 20 miles
3418 Marble Arch Dr - Photo 1 of 1

1d ago

Green Haven house for rent in Pasadena

3418 Marble Arch Dr, Pasadena, MD 21122

In-unit laundry | Outdoor space | Swimming pool

1 bed

1.5 baths

$2,200

House for rent

Available Jun 29

4740 Frederick Ave - Photo 1 of 1

1d ago

House for rent in Shady Side

4740 Frederick Ave, Shady Side, MD 20764

In-unit laundry | Outdoor space | Storage

1 bed

1 bath

$1,800

House for rent

4807 Woods Wharf Rd - Photo 1 of 1

1d ago

House for rent in Shady Side

SINGLE_FAMILY - Bungalow - SHADY SIDE, MD

4807 Woods Wharf Rd, Shady Side, MD 20764

In-unit laundry | Outdoor space | Storage

2 beds

1 bath

$2,495

House for rent

1121 Tyler Ave #1A - Photo 1 of 1

1d ago

House for rent in Annapolis

APARTMENT - ANNAPOLIS, MD

1121 Tyler Ave #1A, Annapolis, MD 21403

In-unit laundry | Air conditioning | Swimming pool

1 bed

1 bath

$2,300

House for rent

1239 Fairfax Ave - Photo 1 of 1

1d ago

House for rent in Deale

House for rent

300 Dixon St #308 - Photo 1 of 1

2d ago

Townhouse for rent in Easton

TOWNHOME - Other - EASTON, MD

300 Dixon St #308, Easton, MD 21601

On-site laundry | Garage parking | Carpet

3 beds

2.5 baths

$2,800

House for rent

209 Winchester Beach Dr - Photo 1 of 1

2d ago

House for rent in Arnold

209 Winchester Beach Dr, Arnold, MD 21409

Outdoor space | Swimming pool | High ceilings

4 beds

4 baths

$8,000

House for rent

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3581 Brickwall Ln #NA - Photo 1 of 1

2d ago

Green Haven house for rent in Pasadena

$2,200 - 3 Bedroom 1 Bathroom House In Pasadena

3581 Brickwall Ln #NA, Pasadena, MD 21122

In-unit laundry | Outdoor space | Storage

3 beds

1 bath

$2,200

House for rent

Available Jun 15

4d ago

Selby-on-the-Bay house for rent in Mayo

SINGLE_FAMILY - Craftsman - EDGEWATER, MD

799 Central Ave E, Mayo, MD 21037

In-unit laundry | Garage parking | Walk-in closets

4 beds

2.5 baths

$3,500

House for rent

5 Waveland Farms Rd - Photo 1 of 1

4d ago

House for rent in Annapolis

SINGLE_FAMILY - Other - ANNAPOLIS, MD

5 Waveland Farms Rd, Annapolis, MD 21409

In-unit laundry | Outdoor space | Storage

4 beds

4 baths

$6,500

House for rent

29670 Old Creek Ln - Photo 1 of 1

5d+ ago

House for rent in Easton

SINGLE_FAMILY - Other - EASTON, MD

29670 Old Creek Ln, Easton, MD 21601

On-site laundry | Outdoor space | Storage

4 beds

2.5 baths

$3,000

House for rent

295 Overleaf Ct - Photo 1 of 1

5d+ ago

House for rent in Arnold

SINGLE_FAMILY - ARNOLD, MD

295 Overleaf Ct, Arnold, MD 21012

In-unit laundry | Garage parking | Hardwood floor

4 beds

2.5 baths

$3,600

House for rent

57 Spa Rd - Photo 1 of 1

5d+ ago

House for rent in Annapolis

SINGLE_FAMILY - Other - ANNAPOLIS, MD

57 Spa Rd, Annapolis, MD 21401

In-unit laundry | Outdoor space | Storage

3 beds

2.5 baths

$4,500

House for rent

Showing 1 - 25 of 25 results
Home > House Rentals in Chester
Updated: June 6, 2026

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Discover houses for rent in Chester, MD

🌇Available house rentals25 houses
💰Best rent deal107 Winchester Ave #107
🍃With outdoor space
Popular amenities, ,
🍽With dishwasher
🏠With photos