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Houses for Rent in Chestertown, MD

Average rent

$2,975

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9919 Augustine Herman Hwy - Photo 1 of 1

6m ago

House for rent in Chestertown

9919 Augustine Herman Highway

9919 Augustine Herman Hwy, Chestertown, MD 21620

In-unit laundry | Outdoor space | Storage

4 beds

2 baths

$2,000

House for rent

Available Apr 15

Listings within 10 miles
151 Hammer Run - Photo 1 of 1

2d ago

House for rent in Centreville

SINGLE_FAMILY - Cape Cod - CENTREVILLE, MD

151 Hammer Run, Centreville, MD 21617

In-unit laundry | Outdoor space | Garage parking

4 beds

3 baths

$3,200

House for rent

501 Main St #4-501 - Photo 1 of 1

5d+ ago

House for rent in Church Hill

SINGLE_FAMILY - Other - CHURCH HILL, MD

501 Main St #4-501, Church Hill, MD 21623

1 bed

1 bath

$1,150

House for rent

718 Church Hill Rd - Photo 1 of 1

5d+ ago

Townhouse for rent in Centreville

TOWNHOME - National - CENTREVILLE, MD

718 Church Hill Rd, Centreville, MD 21617

In-unit laundry | Hardwood floor

2 beds

1 bath

$1,800

House for rent

Nearby rental good for eco-living

$2,600

Queenstown

Nearby rental good for pet owners

$2,100

Middle River

720 Church Hill Rd - Photo 1 of 1

5d+ ago

House for rent in Centreville

APARTMENT - National - CENTREVILLE, MD

720 Church Hill Rd, Centreville, MD 21617

Hardwood floor

3 beds

2 baths

$2,000

House for rent

106 Johnstown Lane #1 - Photo 1 of 1

5d+ ago

House for rent in Centreville

106 Johnstown Lane - 1

106 Johnstown Lane #1, Centreville, MD 21617

In-unit laundry

3 beds

2 baths

$2,000

House for rent

Available Dec 1

Listings within 20 miles
907 Auckland Way - Photo 1 of 1

21h ago

Townhouse for rent in Chester

907 Auckland Way, Chester, MD 21619

In-unit laundry | Outdoor space | Garage parking

3 beds

3 baths

$3,200

House for rent

7500 Main St - Photo 1 of 1

1d ago

House for rent in Queenstown

Detached, Single Family - QUEENSTOWN, MD

7500 Main St, Queenstown, MD 21658

In-unit laundry | Garage parking | Carpet

2 beds

2 baths

$2,200

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.

$2,000

Chestertown

$3,200

Centreville

$1,775

Bowleys Quarters

44 Pocahontas Dr - Photo 1 of 1

3d ago

House for rent in Earleville

44 Pocahantos Drive - -

44 Pocahontas Dr, Earleville, MD 21919

In-unit laundry | Garage parking | Hardwood floor

4 beds

3 baths

$2,995

House for rent

Available Feb 26

7199 Cunning Cir - Photo 1 of 1

5d+ ago

Townhouse for rent in Middle River

3 Bedrooms 3 Bathrooms

7199 Cunning Cir, Middle River, MD 21220

3 beds

3 baths

$2,500

House for rent

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112 W Main St - Photo 1 of 1
New construction

5d+ ago

House for rent in Sudlersville

SINGLE_FAMILY - Rambler - SUDLERSVILLE, MD

112 W Main St, Sudlersville, MD 21668

Garage parking | Dishwasher

3 beds

2 baths

$2,700

House for rent

235 Thompson Ave - Photo 1 of 1

5d+ ago

Townhouse for rent in Queenstown

235 Thompson Ave

235 Thompson Ave, Queenstown, MD 21658

In-unit laundry | Outdoor space | Assigned parking

3 beds

2 baths

$2,600

House for rent

Available Mar 15

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 | Fireplace | Furnished

5 beds

5 baths

$5,500

House for rent

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

815 Seneca Park Rd - Photo 1 of 1
3D tour

3h ago

House for rent in Bowleys Quarters

815 Seneca Park Rd, Bowleys Quarters, MD 21220

Outdoor space | Oven

5 beds

2 baths

$2,390

$2,050

Price drop

House for rent

203 Thompson Ave - Photo 1 of 1

5d+ ago

Townhouse for rent in Queenstown

203 Thompson Ave

203 Thompson Ave, Queenstown, MD 21658

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$2,600

House for rent

Available Apr 1

269 Thompson Ave - Photo 1 of 1

5d+ ago

Townhouse for rent in Queenstown

269 Thompson Ave

269 Thompson Ave, Queenstown, MD 21658

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$2,600

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 | Outdoor space | Garage parking

4 beds

2 baths

$3,295

House for rent

Available Feb 14

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629 Harbour Oak Dr - Photo 1 of 1

5d+ ago

House for rent in Edgewood

629 Harbour Oak Dr, Edgewood, MD 21040

In-unit laundry | Outdoor space | Dishwasher

4 beds

2 baths

$2,200

House for rent

3922 Cutty Sark Rd - Photo 1 of 1
Rent special

5d+ ago

Our team has verified this company

Verified

At Last, This Is What You Have Been Searching For!

3922 Cutty Sark Rd, Bowleys Quarters, MD 21220

3 beds

1 bath

$1,775

House for rent

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 | Storage | Garage parking

3 beds

3 baths

$2,850

House for rent

Explore surrounding listings that match your search:
630 Kingston Rd - Photo 1 of 1

13h ago

Townhouse for rent in Middle River

630 Kingston Rd, Middle River, MD 21220

In-unit laundry | Hardwood floor | Dishwasher

3 beds

2 baths

$1,950

House for rent

Available Mar 1

820 Wingsail Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Joppatowne

TOWNHOME - Contemporary - JOPPA, MD

820 Wingsail Ct, Joppatowne, MD 21085

Garage parking

3 beds

2 baths

$2,100

House for rent

25880 Brookwood Rd - Photo 1 of 1

5d+ ago

House for rent in Greensboro

SINGLE_FAMILY - Rambler - GREENSBORO, MD

25880 Brookwood Rd, Greensboro, MD 21639

In-unit laundry | Outdoor space | Carpet

3 beds

2 baths

$1,800

House for rent

665 Towne Center Dr - Photo 1 of 1

5d+ ago

House for rent in Joppatowne

SINGLE_FAMILY - Other - JOPPA, MD

665 Towne Center Dr, Joppatowne, MD 21085

Outdoor space

3 beds

3 baths

$2,200

House for rent

Showing 1 - 25 of 25 results
Home > House Rentals in Chestertown
Updated: March 3, 2026

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Discover houses for rent in Chestertown, MD

🌇Available house rentals25 houses
💰Best rent deal9919 Augustine Herman Hwy
⭐Popular amenities, ,
🚗With garage parking
🏠With photos