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Apartments for Rent in Chestertown, MD

All rentals

331 Devon Dr - Photo 1 of 1

4d ago

House for rent in Chestertown

Residential Lease, CHESTERTOWN, MD

331 Devon Dr, Chestertown, MD 21620

Garage parking

4 beds

3.5 baths

$2,750

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
23686 L Rd - Photo 1 of 1

4d ago

House for rent in Chestertown

Residential Lease, CHESTERTOWN, MD

23686 L Rd, Chestertown, MD 21620

3 beds

1 bath

$1,700

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
23322 Sandpiper Rd - Photo 1 of 1

5d+ ago

House for rent in Chestertown

23322 Sandpiper Drive

23322 Sandpiper Rd, Chestertown, MD 21620

In-unit laundry | Carpet | Dishwasher

3 beds

2 baths

$1,950

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
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

Garage parking | On-site laundry | Assigned parking

3 beds

1 bath

$1,900

Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.
Listings within 10 miles
11771 Augustine Herman Hwy - Photo 1 of 1

5d+ ago

House for rent in Kennedyville

11771 Augustine Herman Hwy

11771 Augustine Herman Hwy, Kennedyville, MD 21645

In-unit laundry | On-site laundry | Storage

3 beds

2.5 baths

$2,250

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
Listings within 20 miles
907 Olive Branch Ct - Photo 1 of 1

3d ago

Townhouse for rent in Edgewood

Residential Lease, EDGEWOOD, MD

907 Olive Branch Ct, Edgewood, MD 21040

Ceiling fan

3 beds

2.5 baths

$2,000

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
410 Acadia Dr - Photo 1 of 1

4d ago

House for rent in Joppatowne

Residential Lease, JOPPA, MD

410 Acadia Dr, Joppatowne, MD 21085

Garage parking | On-site laundry | Ceiling fan

3 beds

2 baths

$2,700

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
104 Kidwell Ave - Photo 1 of 1

5d+ ago

House for rent in Centreville

104 Kidwell Ave, Centreville, MD 21617

Air conditioning | On-site laundry | Assigned parking

3 beds

3 baths

$2,950

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
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709 Beadlilly Way - Photo 1 of 1
New construction

5d+ ago

Townhouse for rent in Joppatowne

Residential Lease, JOPPA, MD

709 Beadlilly Way, Joppatowne, MD 21085

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

4 beds

2.5 baths

$3,000

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
847 Clover Leaf Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

Residential Lease, EDGEWOOD, MD

847 Clover Leaf Ct, Edgewood, MD 21040

Swimming pool | Deck | Dishwasher

3 beds

2.5 baths

$2,300

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
317 Hackley Dr - Photo 1 of 1
New construction

5d+ ago

Townhouse for rent in Joppatowne

Residential Lease, JOPPA, MD

317 Hackley Dr, Joppatowne, MD 21085

Garage parking

3 beds

3 baths

$2,795

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
509 Foster Knoll Dr - Photo 1 of 1

5d+ ago

Apartment for rent in Joppatowne

509 Foster Knoll Dr, Joppatowne, MD 21085

Air conditioning | Fireplace | Dishwasher

4 beds

2 baths

$2,400

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
109 S Liberty St - Photo 1 of 1

5d+ ago

House for rent in Centreville

109 S Liberty St Centreville

109 S Liberty St, Centreville, MD 21617

In-unit laundry | Balcony | Storage

3 beds

1.5 baths

$1,950

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.

Find sweet deals near Chestertown

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

$2,400

Joppatowne

$1,950

Centreville

$2,100

Centreville

$2,790

Centreville

1030 Old Love Point Rd - Photo 1 of 1

5d+ ago

House for rent in Stevensville

Kent Island Life!

1030 Old Love Point Rd, Stevensville, MD 21666

In-unit laundry | Air conditioning | Garage parking

5 beds

3 baths

$3,650

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
395 S Commerce St - Photo 1 of 1

5d+ ago

House for rent in Centreville

Residential Lease, CENTREVILLE, MD

395 S Commerce St, Centreville, MD 21617

In-unit laundry | Hardwood floor | Dishwasher

3 beds

2 baths

$2,100

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
309 Blue Bay Rd - Photo 1 of 1

4d ago

House for rent in Stevensville

Residential Lease, STEVENSVILLE, MD

309 Blue Bay Rd, Stevensville, MD 21666

In-unit laundry | Garage parking | Swimming pool

4 beds

4.5 baths

$7,000

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
616 Yorkshire Dr - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

Spacious 3-BR, 2.5-BA Townhouse for Rent in Edgewood, MD - Available Nov 2026

616 Yorkshire Dr, Edgewood, MD 21040

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

3 beds

2.5 baths

$2,350

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
129 Encore Ct - Photo 1 of 1
Age restricted

5d+ ago

House for rent in Centreville

Residential Lease, CENTREVILLE, MD

129 Encore Ct, Centreville, MD 21617

In-unit laundry | Garage parking | Swimming pool

2 beds

2 baths

$2,450

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
1915 Graymount Way - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

Beautiful [3BR/2.5BA] Townhome in Trimble Meadows - Available Jan 2027

1915 Graymount Way, Edgewood, MD 21040

In-unit laundry | Hardwood floor | Carpet

3 beds

2.5 baths

$2,200

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
205 Joppa Farm Rd - Photo 1 of 1

5d+ ago

Townhouse for rent in Joppatowne

Residential Lease, JOPPA, MD

205 Joppa Farm Rd, Joppatowne, MD 21085

In-unit laundry | Air conditioning | Garage parking

3 beds

2.5 baths

$2,850

Price dropped $150Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
122 N Main St - Photo 1 of 1

5d+ ago

House for rent in Galena

Residential Lease, GALENA, MD

122 N Main St, Galena, MD 21635

In-unit laundry | Air conditioning | Garage parking

4 beds

2.5 baths

$2,950

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
2806 Captains Cove Ct #NA - Photo 1 of 1

5d+ ago

House for rent in Edgewood

$3,500 - 4 Bedroom 4 Bathroom House In Edgewood With Great Amenities

2806 Captains Cove Ct #NA, Edgewood, MD 21040

In-unit laundry | Air conditioning | Garage parking

4 beds

4 baths

$3,500

Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.
3001 Mahonia Way - Photo 1 of 1

5d+ ago

House for rent in Edgewood

3001 Mahonia Way, Edgewood, MD 21040

Air conditioning | Central heat | Dishwasher

5 beds

3 baths

$2,600

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
804 Mason Rd - Photo 1 of 1

5d+ ago

House for rent in Stevensville

804 Mason Rd, Stevensville, MD 21666

In-unit laundry | Air conditioning | Assigned parking

3 beds

2.5 baths

$3,100

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
1903 Hawthorne Rd - Photo 1 of 1

5d+ ago

House for rent in Edgewood

Residential Lease, EDGEWOOD, MD

1903 Hawthorne Rd, Edgewood, MD 21040

In-unit laundry | Garage parking | Carpet

4 beds

2 baths

$2,800

Price dropped $100Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
Showing 1 - 25 of 25 results
Home > Apartments in Chestertown
Updated: October 28, 2026

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Houses for rent in Chestertown3 rentals

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Chestertown, MD apartments for rent

Average rent in Chestertown, MD

As of today, Chestertown's average rent price is $1,900 per month. See the Chestertown rent report.

Average rent

$1,900

Rentals, last 30 days

16

Average rent by unit type in Chestertown, MD, last 30 days
Unit typeAverage rentvs last year
All bedrooms$1,900/moN/A
1 bedroom$1,215/moN/A
2 bedroom$1,662/moN/A
3 bedroom$2,200/moN/A
Not sure what you can afford? Try our rent calculator

Frequently asked questions

What is the average rent in Chestertown, MD?

The average rent in Chestertown, MD is $1,900 a month. 1-bedrooms average $1,215 and 2-bedrooms $1,662, based on rentals listed on Zumper in the last 30 days. See the Chestertown rent report.

How much rent can I afford in Chestertown, MD?

You'd need to earn about $48,600 a year to afford an average 1-bedroom here ($1,215 a month), with rent at 30% of your income. Try the rent calculator with your own numbers.

Methodology: How we got this data

Zumper’s proprietary rental data fuels our analysis. Rent and market trends and availability are calculated using real-time and 2026 rental inventory and prices.

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.

Looking for apartments in Chestertown, MD near you?

Chestertown, MD rental availability
🔑Available apartment rentals25
💰Best rent deal23686 L Rd
✨Popular amenities, ,
🍽With dishwasher
🏠With photos