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Houses for Rent in Chestertown, MD

All rentals

115 Acorn Dr - Photo 1 of 1

2d ago

Townhouse for rent in Chestertown

115 Acorn Drive

115 Acorn Dr, Chestertown, MD 21620

In-unit laundry | Garage parking | Carpet

2 beds

2.5 baths

$1,950

House for rent

Available Sep 15

22427 Cross Rd - Photo 1 of 1

5d+ ago

House for rent in Chestertown

Residential Lease, CHESTERTOWN, MD

22427 Cross Rd, Chestertown, MD 21620

3 beds

1 bath

$1,600

House for rent

Cedar Point Rd #NA - Photo 1 of 1

5d+ ago

House for rent in Chestertown

3 bedroom 1bath water view farmhouse

Cedar Point Rd #NA, Chestertown, MD 21620

On-site laundry | Storage | Garage parking

3 beds

1 bath

$1,900

House for rent

Available Sep 6

Charming Farmhouse with River Views & Country Vibes

Embrace rural living in this delightful 3-bedroom, 1-bathroom farmhouse with 1,800 sq ft of character. Enjoy breathtaking sunsets over the Chester River from your private farmland. Features include beautiful hardwood floors, ample storage, and on-site laundry. Just minutes from downtown Chestertown, this unique home offers a tranquil escape. Perfect for those seeking peace and charm in a picturesque setting.

206 N Mill St - Photo 1 of 1

5d+ ago

House for rent in Chestertown

Residential Lease, CHESTERTOWN, MD

206 N Mill St, Chestertown, MD 21620

In-unit laundry | Outdoor space | Storage

3 beds

2.5 baths

$1,950

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

$1,750

House for rent

Available Sep 1

Nearby rental good for eco-living

$2,100

Edgewood

Nearby rental good for wfh

Listings within 20 miles
1473 Charlestown Dr - Photo 1 of 1

5d+ ago

House for rent in Edgewood

1473 Charlestown Dr, Edgewood, MD 21040

In-unit laundry | Dishwasher | Oven

3 beds

1.5 baths

$2,100

House for rent

210 Trails Way - Photo 1 of 1
Age restricted

5d+ ago

Townhouse for rent in Joppatowne

Residential Lease, JOPPA, MD

210 Trails Way, Joppatowne, MD 21085

Garage parking

3 beds

2.5 baths

$2,600

House for rent

225 Joppa Farm Rd - Photo 1 of 1

5d+ ago

Townhouse for rent in Joppatowne

225 Joppa Farm Rd, Joppatowne, MD 21085

In-unit laundry | Garage parking | Hardwood floor

4 beds

3.5 baths

$3,500

House for rent

Available Aug 10

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3 Lasonia Ct - Photo 1 of 1

2d ago

Townhouse for rent in Edgewood

House for rent

102 Weedon St - Photo 1 of 1

5d+ ago

House for rent in Centreville

102 Weedon Street

102 Weedon St, Centreville, MD 21617

In-unit laundry | Outdoor space | Storage

2 beds

1 bath

$1,650

House for rent

Available Oct 15

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Find sweet deals near Chestertown

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

$1,600

Chestertown

$2,650

Stevensville

$2,885

Centreville

310 Del Rhodes Ave - Photo 1 of 1

5d+ ago

Townhouse for rent in Queenstown

TOWNHOME - Colonial - QUEENSTOWN, MD

310 Del Rhodes Ave, Queenstown, MD 21658

In-unit laundry | Storage | Garage parking

3 beds

2.5 baths

$2,400

House for rent

1904 Eloise Ln - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

Residential Lease, EDGEWOOD, MD

1904 Eloise Ln, Edgewood, MD 21040

Outdoor space

3 beds

1.5 baths

$1,750

House for rent

377 Hackley Dr - Photo 1 of 1
New construction

5d+ ago

Townhouse for rent in Joppatowne

TOWNHOME - Other - JOPPA, MD

377 Hackley Dr, Joppatowne, MD 21085

On-site laundry | Outdoor space | Garage parking

3 beds

2.5 baths

$2,850

House for rent

627 Davol Rd - Photo 1 of 1

5d+ ago

House for rent in Stevensville

Residential Lease, STEVENSVILLE, MD

627 Davol Rd, Stevensville, MD 21666

In-unit laundry | Outdoor space | Swimming pool

4 beds

2 baths

$2,750

$2,650

Price drop

House for rent

2620 Love Point Rd - Photo 1 of 1

4d ago

House for rent in Stevensville

Residential Lease, STEVENSVILLE, MD

2620 Love Point Rd, Stevensville, MD 21666

In-unit laundry | Fireplace | Furnished

5 beds

5 baths

$4,800

$4,500

Price drop

House for rent

446 Railroad Ave - Photo 1 of 1

5d+ ago

Townhouse for rent in Centreville

TOWNHOME - Cape Cod - CENTREVILLE, MD

446 Railroad Ave, Centreville, MD 21617

2 beds

1 bath

$1,650

House for rent

116 Walnut St - Photo 1 of 1

5d+ ago

House for rent in Centreville

SINGLE_FAMILY - Cape Cod - CENTREVILLE, MD

116 Walnut St, Centreville, MD 21617

Storage | Air conditioning | Hardwood floor

3 beds

1 bath

$2,000

House for rent

6808 Main St - Photo 1 of 1

4d ago

House for rent in Queenstown

Residential Lease, QUEENSTOWN, MD

6808 Main St, Queenstown, MD 21658

Hardwood floor

3 beds

1 bath

$2,350

$2,200

Price drop

House for rent

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119 Watson Rd - Photo 1 of 1

5d+ ago

House for rent in Centreville

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

Residential Lease, CENTREVILLE, MD

212 Frederick Dr, Centreville, MD 21617

In-unit laundry | Outdoor space | Storage

4 beds

2.5 baths

$2,885

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

704 Saint Peters Ct - Photo 1 of 1

4d ago

Townhouse for rent in Edgewood

704 Saint Peters Ct, Edgewood, MD 21040

In-unit laundry | Outdoor space | Air conditioning

3 beds

2.5 baths

$1,895

House for rent

962 Topview Dr - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

House for rent

1830 Eloise Ln - Photo 1 of 1
3D tour

5d+ ago

Townhouse for rent in Edgewood

1830 Eloise Ln, Edgewood, MD 21040

In-unit laundry | Outdoor space | Dishwasher

3 beds

1.5 baths

$1,800

House for rent

Explore surrounding listings that match your search:
717 Pickerel Pl - Photo 1 of 1
New construction

5d+ ago

Townhouse for rent in Joppatowne

Residential Lease, JOPPA, MD

717 Pickerel Pl, Joppatowne, MD 21085

On-site laundry | Garage parking | Walk-in closets

4 beds

2.5 baths

$2,500

House for rent

Showing 1 - 25 of 25 results
Home > House Rentals in Chestertown
Updated: August 31, 2026

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Apartments for rent in Chestertown5 rentals

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Discover houses for rent in Chestertown, MD

🌇Available house rentals25 houses
💰Best rent deal22427 Cross Rd
🍃With outdoor space
⭐Popular amenities, ,
🍽With dishwasher
🚗With garage parking
🏠With photos