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Apartments for Rent in Chestertown, MD

Average rent

$2,225
increased by9%

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24731 Langford Rd #B - Photo 1 of 1

5d+ ago

Apartment for rent in Chestertown

Private country apartment

24731 Langford Rd #B, Chestertown, MD 21620

In-unit laundry | On-site laundry | Carpet

1 bed

1 bath

$1,200

Apartment for rent

Available Aug 15

1-bed creekside apartment with utilities included

Set in Chestertown, MD, this 1-bed, 1-bath apartment sits on a creek with kayaking and fishing access. The 790 sqft layout features a large kitchen, spacious bathroom, and shared laundry room with all utilities and fiber optic internet included in rent - a fit for remote workers. Recently updated with fresh paint and professionally cleaned carpets, plus outdoor grilling area and off-street parking.

104 Cedar St - Photo 1 of 1

5d+ ago

House for rent in Chestertown

SINGLE_FAMILY - Colonial - CHESTERTOWN, MD

104 Cedar St, Chestertown, MD 21620

Garage parking | Ceiling fan

3 beds

2.5 baths

$2,600

House for rent

Colonial 3-bed house near college and downtown

Located in Chestertown, MD, this colonial-style 3-bed, 2.5-bath house sits close to the college, downtown, and local shopping. The 2,612 sqft two-story layout features central air, ceiling fans, and garage parking. Brick and combination exterior adds curb appeal to this no-pet, no-smoking rental available June 1st.

Listings within 20 miles
212 Bohemia Church Rd - Photo 1 of 1

1h ago

House for rent in Warwick

212 Bohemia Church Rd, Warwick, MD 21912

In-unit laundry | Garage parking | Balcony

3 beds

3 baths

$2,700

House for rent

Available Jul 1

105 Dogwood Dr - Photo 1 of 1

5d+ ago

House for rent in Galena

SINGLE_FAMILY - Rambler - GALENA, MD

105 Dogwood Dr, Galena, MD 21635

In-unit laundry | Garage parking | Walk-in closets

3 beds

2 baths

$2,500

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 | Hardwood floor | Ceiling fan

3 beds

1.5 baths

$2,600

House for rent

1046 Agate Dr #1 - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

1046 Agate Drive - 1

1046 Agate Dr #1, Edgewood, MD 21040

Air conditioning | On-site laundry | Balcony

4 beds

2.5 baths

$2,150

House for rent

Available Jun 1

25 2nd Ave - Photo 1 of 1
New construction

4d ago

House for rent in Earleville

Detached, Single Family - EARLEVILLE, MD

25 2nd Ave, Earleville, MD 21919

Outdoor space

3 beds

2 baths

$2,495

$2,395

Price drop

House for rent

2816 Profitt Path - Photo 1 of 1

5d+ ago

House for rent in Edgewood

2816 Profitt Path, Edgewood, MD 21040

In-unit laundry | On-site laundry | Hardwood floor

4 beds

3 baths

$2,950

House for rent

Available May 6

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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

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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

$1,400

Apartment 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

$1,250

Condo 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

1501 Saint Christopher Ct - Photo 1 of 1

3d 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

$2,450

$2,200

Price drop

House for rent

Find sweet deals near Chestertown

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

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

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8 Lasonia Ct - Photo 1 of 1
3D tour

5d+ ago

House for rent in Edgewood

8 Lasonia Ct/ Large 3 bedroom 2.5 bath house

8 Lasonia Ct, Edgewood, MD 21040

Garage parking | On-site laundry | Storage

3 beds

3 baths

$2,195

House for rent

313 Winterberry Dr - Photo 1 of 1

5d+ ago

House for rent in Edgewood

House for rent

903 Woodbridge Ct #D - Photo 1 of 1

5d+ ago

Apartment for rent in Edgewood

903 Woodbridge Ct #D, Edgewood, MD 21040

In-unit laundry | On-site laundry | Storage

2 beds

1 bath

$1,500

Apartment for rent

Available Jun 30

512 Scholar Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

512 Scholar Court Edgewood, Maryland 21040

512 Scholar Ct, Edgewood, MD 21040

In-unit laundry | Air conditioning | On-site laundry

3 beds

2.5 baths

$2,150

House for rent

Available Jul 1

6207 Edgewood Rd #C - Photo 1 of 1

5d+ ago

Condo for rent in Edgewood

Condo for rent

1945 Graymount Way - Photo 1 of 1

5d+ ago

Townhouse for rent in Edgewood

1945 Graymount Way, Edgewood, MD 21040

In-unit laundry | Air conditioning | On-site laundry

3 beds

2 baths

$2,195

House for rent

313 Garnett Rd - Photo 1 of 1

5d+ ago

House for rent in Joppatowne

313 Garnett Rd, Joppatowne, MD 21085

In-unit laundry | Air conditioning | Garage parking

4 beds

3 baths

$2,695

House for rent

Showing 1 - 25 of 25 results
Home > Apartments in Chestertown
Updated: June 10, 2026

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Learn more about renting in Chestertown, MD

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.

What kinds of apartments are available to rent in Chestertown, MD?

Chestertown is a small but active rental market with an average of 7 listings available per month. Three-bedroom apartments make up the largest share at 43% of inventory, while two-bedroom units account for 29%. Studios and one-bedroom apartments are less common, each representing only 14% of monthly listings.

Chestertown apartments cater to renters who value convenient home features. Dishwashers lead the amenity list, available in 57% of listings. In-unit laundry is equally prevalent at 57% of apartments, offering residents the convenience of private washing facilities. On-site laundry facilities also appear in 57% of listings, providing additional options for those without in-unit access. These averages offer a useful snapshot, though the live market may shift.

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 2026 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 1 bedroom apartment rental in Chestertown is 790 square feet. The average size of a 3 bedroom apartment rental in Chestertown is 2612 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 deal24731 Langford Rd #B
Popular amenities, ,
🍽With dishwasher
🏠With photos