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Apartments for Rent in Chestertown, MD

Average rent

$2,500
increased by44%

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Brices Mill Rd #NA - Photo 1 of 1

5d+ ago

House for rent in Chestertown

$2,600 - 4 Bedroom 3 Bathroom House In Chestertown

Brices Mill Rd #NA, Chestertown, MD 21620

In-unit laundry | Air conditioning | Garage parking

4 beds

3 baths

$2,600

House for rent

Available Apr 1

Serene Country Home with Spacious Living Areas

Surrounded by tranquil farmland yet just minutes from downtown Chestertown, this spacious 4-bedroom, 2.5-bath home features a well-equipped kitchen with a breakfast nook and a separate dining room. Cozy up by the wood-burning stove in the living room during winter nights. With plentiful parking, an attached garage, and a detached garage, this property blends comfort with country charm. Ample views of nature enhance the peaceful ambiance throughout the home.

Listings within 10 miles
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

Listings within 20 miles
2816 Profitt Path - Photo 1 of 1

3h ago

House for rent in Edgewood

Single Family home

2816 Profitt Path, Edgewood, MD 21040

In-unit laundry | Garage parking | Balcony

4 beds

3 baths

$2,900

House for rent

Available May 1

2007 Bayberry Rd - Photo 1 of 1

14h ago

House for rent in Edgewood

In-unit laundry | Air conditioning | Dishwasher

5 beds

2 baths

$2,395

House for rent

499 Berkshire Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Joppatowne

4 Bedrooms 2.5 Bathrooms, Joppa MD

499 Berkshire Ct, Joppatowne, MD 21085

Storage | Dishwasher | Outdoor space

4 beds

2.5 baths

$2,200

House for rent

6209 Edgewood Rd #C - Photo 1 of 1

5d+ ago

Condo for rent in Edgewood

Condo for rent

2842 Beckon Dr #1 - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

2842 Beckon Drive - 1

2842 Beckon Dr #1, Edgewood, MD 21040

On-site laundry

4 beds

1.5 baths

$2,100

House for rent

Available May 1

722 Church Hill Rd - Photo 1 of 1

5d+ ago

Apartment for rent in Centreville

SINGLE_FAMILY - National - CENTREVILLE, MD

722 Church Hill Rd, Centreville, MD 21617

Hardwood floor | Ceiling fan | Dishwasher

1 bed

1 bath

$1,500

Apartment for rent

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1523 Charlestown Dr - Photo 1 of 1

4d ago

Townhouse for rent in Edgewood

1523 Charlestown Dr, Edgewood, MD 21040

In-unit laundry | Carpet | Dishwasher

3 beds

1.5 baths

$1,595

House for rent

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

5d+ ago

Condo for rent in Edgewood

CONDOS - Contemporary - EDGEWOOD, MD

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

In-unit laundry | Garage parking | Ceiling fan

2 beds

1 bath

$1,400

Condo for rent

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619 Hartwood Ln - Photo 1 of 1

5d+ ago

House for rent in Edgewood

4 beds

1.5 baths

$2,400

$2,300

Price drop

House for rent

3184 Ebbtide Dr - Photo 1 of 1

5d+ ago

House for rent in Edgewood

SINGLE_FAMILY - EDGEWOOD, MD

3184 Ebbtide Dr, Edgewood, MD 21040

Garage parking | Hardwood floor

3 beds

3 baths

$2,600

House for rent

Find sweet deals near Chestertown

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

980 Topview Dr - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

House for rent

106 Blenny Ln - Photo 1 of 1

5d+ ago

Townhouse for rent in Chester

TOWNHOME - Other - CHESTER, MD

106 Blenny Ln, Chester, MD 21619

Garage parking | Swimming pool | Fitness center

3 beds

3 baths

$2,899

House for rent

2019 Cherry Rd - Photo 1 of 1

5d+ ago

House for rent in Edgewood

4 beds

2 baths

$2,395

$2,295

Price drop

House for rent

1772 Judy Way - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

Newly Renovated 3 bed 1.5 bath Townhome in Judy Way

1772 Judy Way, Edgewood, MD 21040

Fireplace | Dishwasher | Microwave

3 beds

1.5 baths

$2,195

House for rent

820 Wingsail Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Joppatowne

TOWNHOME - Contemporary - JOPPA, MD

820 Wingsail Ct, Joppatowne, MD 21085

In-unit laundry | Garage parking

3 beds

2.5 baths

$2,000

House for rent

2828 Beckon Dr - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

TOWNHOME - Other - EDGEWOOD, MD

2828 Beckon Dr, Edgewood, MD 21040

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

3 beds

2.5 baths

$2,300

House for rent

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1501 Saint Christopher Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

TOWNHOME - Colonial - EDGEWOOD, MD

1501 Saint Christopher Ct, Edgewood, MD 21040

Air conditioning | Walk-in closets | Outdoor space

4 beds

2 baths

$2,500

House for rent

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 Ln #1 - Photo 1 of 1

5d+ ago

House for rent in Centreville

106 Johnstown Lane - 1

106 Johnstown Ln #1, Centreville, MD 21617

In-unit laundry

3 beds

2.5 baths

$2,000

House for rent

Available Dec 1

1 Edgewood Road #1 - Photo 1 of 1

5d+ ago

Apartment for rent in Edgewood

4048 Edgewood Road - 1

1 Edgewood Road #1, Edgewood, MD 21040

1 bed

1 bath

$1,150

Apartment for rent

Available Nov 26

905 Swallow Crest Ct #E - Photo 1 of 1

5d+ ago

Condo for rent in Edgewood

905 Swallow Crest Ct #E, Edgewood, MD 21040

Swimming pool | Dishwasher | Oven

2 beds

1 bath

$1,495

Condo for rent

231 Joppa Farm Rd - Photo 1 of 1
New construction

5d+ ago

Townhouse for rent in Joppatowne

TOWNHOME - Other - JOPPA, MD

231 Joppa Farm Rd, Joppatowne, MD 21085

Garage parking | Fitness center | Walk-in closets

4 beds

3.5 baths

$3,200

House for rent

313 Winterberry Dr - Photo 1 of 1

5d+ ago

House for rent in Edgewood

House for rent

Showing 1 - 25 of 25 results
Home > Apartments in Chestertown
Updated: May 5, 2026

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Learn more about renting in Chestertown, MD

1

Local insights: What it's like to live in Chestertown, MD

Chestertown, MD, offers a relaxed atmosphere with scenic views and a vibrant arts scene, appealing to those who enjoy cultural events and outdoor activities. Residents appreciate the historic charm of the downtown area, with its local shops and eateries that foster a sense of connection. However, some locals express frustrations about limited nightlife options and a lack of public transportation, which can make it challenging for renters who rely on these amenities. Overall, the quaint surroundings are cherished, even if certain conveniences might leave something to be desired.

Chestertown, MD apartment availability

Chestertown's rental market is relatively small, with an average of 7 listings available per month. The most common apartment sizes are 3-bedroom units, making up 43% of the market, followed by 1-bedroom and 2-bedroom units, each accounting for 29% of the market. Studios are relatively scarce. When it comes to amenities, air conditioning is a common feature, available in 71% of listings. In-unit laundry and dishwashers are also available in about 57% of apartments, making them a desirable perk for renters. Overall, renters in Chestertown will need to be flexible with their expectations and act quickly when a suitable apartment becomes available.

Methodology: How we got this data

Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2024 rental inventory and prices.

Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.

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.

Apartment rentals Chestertown, MD FAQ

What is the average size of an apartment in Chestertown, MD?

The average size of a 2 bedroom apartment rental in Chestertown is 670 square feet. The average size of a 3 bedroom apartment rental in Chestertown is 1890 square feet.

Can I afford an apartment for rent in Chestertown, MD?

To help you better understand how much rent you can afford, check out Zumper's rent calculator. Our rent calculator can help you learn more about Chestertown average rent prices.

Looking for apartments in Chestertown, MD near you?

🔑Available apartment rentals25
💰Best rent dealBrices Mill Rd #NA
Popular amenities, ,
🍽With dishwasher
🏠With photos