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Apartments for Rent in Chestertown, MD

Average rent

$2,000
increased by44%

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509 Cannon St - Photo 1 of 1

5d+ ago

House for rent in Chestertown

SINGLE_FAMILY - Bungalow - CHESTERTOWN, MD

509 Cannon St, Chestertown, MD 21620

2 beds

1 bath

$1,400

House for rent

Cozy Updated Bungalow with Off-Street Parking

This charming 2-bedroom, 1-bath bungalow features thoughtful updates and a comfortable layout. Enjoy year-round comfort with a brand-new HVAC system and convenient off-street parking. Perfect for those seeking a cozy retreat!

9919 Augustine Herman Hwy - Photo 1 of 1

5d+ ago

House for rent in Chestertown

9919 Augustine Herman Highway

9919 Augustine Herman Hwy, Chestertown, MD 21620

In-unit laundry | Storage | Carpet

4 beds

2 baths

$2,000

House for rent

Available Apr 15

Secluded Serenity with Scenic Creek Views

This 1,680 sq. ft. home on a family farm features 4 bedrooms and 2 baths, offering a peaceful retreat. Enjoy wildlife sightings from the outdoor deck while basking in the tranquility of nature. A full basement provides ample storage, making it ideal for those seeking solitude and scenic beauty. A perfect blend of spaciousness and seclusion awaits.

202 High St #E - Photo 1 of 1

5d+ ago

Apartment for rent in Chestertown

Large, renovated 2 br in the middle of downtown Chestertown

202 High St #E, Chestertown, MD 21620

In-unit laundry | Storage | Dishwasher

2 beds

1 bath

$2,000

Apartment for rent

Available Jun 1

Bright & Modern Apartment in Downtown Chestertown

Newly remodeled 2-bedroom apartment featuring an open kitchen/living/dining area, filled with natural light. Modern kitchen equipped with stainless appliances and granite counters. Ample storage and in-unit washer/dryer enhance convenience. Enjoy one off-street parking spot. Located steps from local favorites like The Kitchen and Evergrain Bakery, this residence offers a perfect blend of comfort and city living.

151 Hammer Run - Photo 1 of 1

5d+ ago

House for rent in Centreville

SINGLE_FAMILY - Cape Cod - CENTREVILLE, MD

151 Hammer Run, Centreville, MD 21617

In-unit laundry | Garage parking | Swimming pool

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

113 Henry Stoupe Way - Photo 1 of 1

3d ago

House for rent in Chester

SINGLE_FAMILY - Colonial - CHESTER, MD

113 Henry Stoupe Way, Chester, MD 21619

In-unit laundry | Garage parking | Swimming pool

3 beds

2 baths

$3,500

House for rent

721 Main St #204 - Photo 1 of 1

5d+ ago

Apartment for rent in Stevensville

721 Main St #204, Stevensville, MD 21666

In-unit laundry | Dishwasher | Microwave

2 beds

1 bath

$1,850

Apartment for rent

Available Apr 1

26-C Queen Anne Way - Photo 1 of 1

5d+ ago

Apartment for rent in Chester

Condo - CHESTER, MD

26-C Queen Anne Way, Chester, MD 21619

On-site laundry | Swimming pool | On-site management

2 beds

1 bath

$2,300

Apartment for rent

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230 Corsica Neck Rd - Photo 1 of 1

5d+ ago

House for rent in Centreville

230 Corsica Neck Rd

230 Corsica Neck Rd, Centreville, MD 21617

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

3 beds

2 baths

$2,500

House for rent

Available Apr 1

907 Auckland Way - Photo 1 of 1

5d+ ago

Townhouse for rent in Chester

Condo - CHESTER, MD

907 Auckland Way, Chester, MD 21619

In-unit laundry | Furnished | Garage parking

3 beds

3 baths

$3,200

House for rent

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In-Unit Laundry

Air Conditioning

Dishwasher

Assigned Parking

44 Pocahontas Dr - Photo 1 of 1

5d+ ago

House for rent in Earleville

44 Pocahontas Drive - -

44 Pocahontas Dr, Earleville, MD 21919

In-unit laundry | Hardwood floor | Fireplace

4 beds

3 baths

$2,995

$2,595

Price drop

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

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

170 Harrier Way - Photo 1 of 1
Age restricted

5d+ ago

Condo for rent in Chester

Condo - CHESTER, MD

170 Harrier Way, Chester, MD 21619

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

2 beds

2 baths

$3,700

Condo for rent

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 | Furnished | Ceiling fan

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

Find sweet deals near Chestertown

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

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

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235 Jessica Lyn Ave - Photo 1 of 1
New construction

5d+ ago

Townhouse for rent in Stevensville

235 Jessica Lyn Ave

235 Jessica Lyn Ave, Stevensville, MD 21666

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

4 beds

3 baths

$3,500

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 | Air conditioning | Garage parking

4 beds

2 baths

$3,295

House for rent

Available Feb 14

Bay Manor- Residential - Photo 1 of 1

5d+ ago

8.6

Very good

Bay Manor- Residential

214 Pier 1 Rd, Stevensville, MD 21666

In-unit laundry | Air conditioning | Balcony

Studio–2 beds

1–2 baths

$1,950–$3,450

Condo for rent

2019 Cherry Rd - Photo 1 of 1

1d ago

House for rent in Edgewood

House for rent

1576 Bay Head Rd - Photo 1 of 1

2d ago

House for rent in Annapolis

SINGLE_FAMILY - Craftsman, Colonial - ANNAPOLIS, MD

1576 Bay Head Rd, Annapolis, MD 21409

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

6 beds

5 baths

$14,000

House for rent

1913 Newhaven Dr - Photo 1 of 1

3d ago

Townhouse for rent in Essex

Quiet town home community close to the water

1913 Newhaven Dr, Essex, MD 21221

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

4 beds

2 baths

$3,400

House for rent

Available Apr 1

504 Crisfield Rd - Photo 1 of 1

5d+ ago

House for rent in Bowleys Quarters

SINGLE_FAMILY - Rambler - BALTIMORE, MD

504 Crisfield Rd, Bowleys Quarters, MD 21220

On-site laundry | Hardwood floor | Fireplace

3 beds

2 baths

$2,900

House for rent

Showing 1 - 25 of 25 results
Home > Apartments in Chestertown
Updated: March 16, 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 789 square feet. The average size of a 3 bedroom apartment rental in Chestertown is 1097 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 deal501 Main St #4-501
Popular amenities, ,
🍽With dishwasher
🏠With photos