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Houses for Rent in Chestertown, MD

Average rent

$2,000

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129A Manor Ave - Photo 1 of 1

5d+ ago

House for rent in Chestertown

3 Bedroom 2 Bath Rancher for Rent

129A Manor Ave, Chestertown, MD 21620

In-unit laundry | Storage | Garage parking

3 beds

2 baths

$2,000

House for rent

Available Jul 15

Cozy Home with New HVAC and Detached Garage

This charming 3-bedroom, 2-bath home is ready for you with a brand new HVAC system ensuring year-round comfort. The interior is spacious and welcoming, complemented by a detached 1-bay garage perfect for storage or a workshop. Ideal for those seeking comfort and functionality in a convenient location. Enjoy the benefits of a low-maintenance lifestyle in this move-in ready residence.

222 Mount Vernon Ave #NA - Photo 1 of 1

5d+ ago

House for rent in Chestertown

$2,950 - 4 Bed, 2 Bath Historic Home in Heart of Chestertown

222 Mount Vernon Ave #NA, Chestertown, MD 21620

Outdoor space | Assigned parking | High ceilings

4 beds

2 baths

$2,950

$2,800

Price drop

House for rent

Available Jul 1

351 Calvert St - Photo 1 of 1

5d+ ago

Townhouse for rent in Chestertown

TOWNHOME - CHESTERTOWN, MD

351 Calvert St, Chestertown, MD 21620

Outdoor space | Ceiling fan

3 beds

1 bath

$2,000

House for rent

8890 Fairlee Rd - Photo 1 of 1

5d+ ago

House for rent in Chestertown

SINGLE_FAMILY - Rambler - CHESTERTOWN, MD

8890 Fairlee Rd, Chestertown, MD 21620

In-unit laundry | Hardwood floor | Dishwasher

3 beds

2 baths

$2,500

House for rent

109 Fairview Dr - Photo 1 of 1

5d+ ago

House for rent in Chestertown

Fairview

109 Fairview Dr, Chestertown, MD 21620

In-unit laundry | Outdoor space | Carpet

3 beds

1 bath

$1,900

House for rent

Available Aug 1

Listings within 20 miles
5807 Blue Claw Ct - Photo 1 of 1

5d+ ago

House for rent in Rock Hall

SINGLE_FAMILY - Other - ROCK HALL, MD

5807 Blue Claw Ct, Rock Hall, MD 21661

In-unit laundry | Storage | Garage parking

4 beds

3 baths

$3,000

House for rent

1322 Harford Square Dr #NA - Photo 1 of 1

23h ago

House for rent in Edgewood

1322 Harford Square Dr #NA, Edgewood, MD 21040

In-unit laundry | Outdoor space | Assigned parking

3 beds

3 baths

$2,300

House for rent

Available Jul 15

702 Cloverfields Dr - Photo 1 of 1

5d+ ago

House for rent in Stevensville

SINGLE_FAMILY - Other - STEVENSVILLE, MD

702 Cloverfields Dr, Stevensville, MD 21666

In-unit laundry | Outdoor space | Garage parking

4 beds

2.5 baths

$2,850

House for rent

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119 Watson Rd - Photo 1 of 1

5d+ ago

House for rent in Centreville

Detached, Single Family - CENTREVILLE, MD

119 Watson Rd, Centreville, MD 21617

On-site laundry | Outdoor space | High ceilings

4 beds

3 baths

$4,300

House for rent

212 Frederick Dr - Photo 1 of 1

5d+ ago

House for rent in Centreville

SINGLE_FAMILY - Colonial - CENTREVILLE, MD

212 Frederick Dr, Centreville, MD 21617

In-unit laundry | Outdoor space | Storage

4 beds

2.5 baths

$2,950

House for rent

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Find sweet deals near Chestertown

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

$1,900

Chestertown

$2,850

Stevensville

$2,950

Centreville

$2,200

Joppatowne

137 Warbler Way - Photo 1 of 1
New construction

5d+ ago

House for rent in Chester

SINGLE_FAMILY - Rambler - CHESTER, MD

137 Warbler Way, Chester, MD 21619

In-unit laundry | Storage | Garage parking

2 beds

2 baths

$4,300

House for rent

2842 Beckon Dr - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

TOWNHOME - Other - EDGEWOOD, MD

2842 Beckon Dr, Edgewood, MD 21040

In-unit laundry | Fitness center | Ceiling fan

4 beds

2 baths

$2,100

House for rent

927 Pirates Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

927 Pirates Ct, Edgewood, MD 21040

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$2,000

House for rent

Available Jun 22

1553 Charlestown Dr - Photo 1 of 1

6h ago

Townhouse for rent in Edgewood

1553 Charlestown Dr, Edgewood, MD 21040

Air conditioning | On-site management

3 beds

1 bath

$1,945

$1,745

Price drop

House for rent

3908 Love Ave - Photo 1 of 1

5d+ ago

House for rent in Edgewood

SINGLE_FAMILY - Other - EDGEWOOD, MD

3908 Love Ave, Edgewood, MD 21040

Storage

4 beds

2 baths

$2,300

House for rent

1424 Saint Michael Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

1424 Saint Michael Ct, Edgewood, MD 21040

Dishwasher | Microwave | Oven

3 beds

1.5 baths

$1,995

House for rent

705 Bayberry Rd - Photo 1 of 1

5d+ ago

House for rent in Edgewood

SINGLE_FAMILY - Ranch - EDGEWOOD, MD

705 Bayberry Rd, Edgewood, MD 21040

In-unit laundry | Outdoor space | Hardwood floor

3 beds

1.5 baths

$2,600

House for rent

25 2nd Ave - Photo 1 of 1
New construction

3d ago

House for rent in Earleville

Detached, Single Family - EARLEVILLE, MD

25 2nd Ave, Earleville, MD 21919

Outdoor space

3 beds

2 baths

$2,195

$2,000

Price drop

House for rent

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499 Berkshire Ct - Photo 1 of 1

1d ago

Townhouse for rent in Joppatowne

4 Bedrooms 2.5 Bathrooms, Joppa MD

499 Berkshire Ct, Joppatowne, MD 21085

Outdoor space | Storage | Dishwasher

4 beds

2.5 baths

$2,200

House for rent

1703 Fountain Rock Way Unit B #1703B - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

CONDOS - Contemporary - EDGEWOOD, MD

1703 Fountain Rock Way Unit B #1703B, Edgewood, MD 21040

In-unit laundry | Outdoor space | Garage parking

2 beds

1 bath

$1,250

House for rent

1841 Graymount Way - Photo 1 of 1

5d+ ago

House for rent in Edgewood

1841 Graymount Way, Edgewood, MD 21040

On-site laundry | Storage | Furnished

1 bed

1 bath

$1,200

House for rent

Available Jun 16

8 Lasonia Ct - Photo 1 of 1

1d ago

House for rent in Edgewood

8 Lasonia Ct/ Large 3 bedroom 2.5 bath house

8 Lasonia Ct, Edgewood, MD 21040

On-site laundry | Outdoor space | Storage

3 beds

3 baths

$2,095

House for rent

962 Topview Dr - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

House for rent

Showing 1 - 23 of 23 results
Home > House Rentals in Chestertown
Updated: July 16, 2026

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Apartments for rent in Chestertown6 rentals

6 rentals

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Discover houses for rent in Chestertown, MD

🌇Available house rentals23 houses
💰Best rent deal109 Fairview Dr
🍃With outdoor space
⭐Popular amenities, ,
👚With laundry facilities
🍽With dishwasher
🚗With garage parking
🏠With photos