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Apartments for Rent in Chestertown, MD

Average rent

$2,800
increased by59%

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129 Manor Avenue - Photo 1 of 1

5d+ ago

House for rent in Chestertown

3 Bedroom 2 Bath Rancher for Rent

129 Manor Avenue, Chestertown, MD 21620

In-unit laundry | Garage parking | Storage

3 beds

2 baths

$2,000

House for rent

Available Jan 15

Charming 3-Bed Home with Detached Garage

This welcoming 3-bedroom, 2-bath home features fresh paint and a brand-new HVAC system, ensuring year-round comfort. The spacious interior is perfect for comfortable living, while the detached 1-bay garage offers ample storage or workshop space. Ideally situated for convenience, this home encompasses comfort and functionality for a delightful living experience.

300 Hilltop Ln - Photo 1 of 1

5d+ ago

Townhouse for rent in Chestertown

TOWNHOME - Colonial - CHESTERTOWN, MD

300 Hilltop Ln, Chestertown, MD 21620

3 beds

2 baths

$2,000

House for rent

Renovated Townhouse with Private Patio Retreat

This charming end-unit townhouse features 3 bedrooms and 2.5 bathrooms in a freshly renovated space spanning 1,200 square feet. The updated kitchen boasts freshly painted cabinets and brand-new appliances, while new flooring throughout gives a modern touch. Relax on the private patio, perfect for outdoor gatherings. Conveniently located just minutes from downtown Chestertown, offering easy access to shopping and dining for a vibrant lifestyle.

118 North Water Street #3 - Photo 1 of 1

5d+ ago

Apartment for rent in Chestertown

118 North Water Street

118 North Water Street #3, Chestertown, MD 21620

In-unit laundry | Hardwood floor

2 beds

1 bath

$1,400

Apartment for rent

Available Dec 15

Charming Water View Apartment with Modern Comforts

Enjoy stunning water views in this pet-friendly 2-bedroom, 1-bath apartment, ideally located just a stroll away from downtown’s shops and eateries. This second-floor unit features hardwood floors, HVAC, and in-unit laundry for convenience. Perfect for those seeking a blend of comfort and vibrant community living!

10546 Worton Road - Photo 1 of 1

3d ago

House for rent in Worton

SINGLE_FAMILY - Ranch - WORTON, MD

10546 Worton Road, Worton, MD 21678

Garage parking | Ceiling fan | Fireplace

4 beds

2 baths

$2,600

House for rent

501 Main Street #4-501 - Photo 1 of 1

5d+ ago

House for rent in Church Hill

SINGLE_FAMILY - Other - CHURCH HILL, MD

501 Main Street #4-501, Church Hill, MD 21623

1 bed

1 bath

$1,250

House for rent

210 Scarlet Ln #E3 - Photo 1 of 1

17h ago

Townhouse for rent in Stevensville

210 Scarlet Ln #E3, Stevensville, MD 21666

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

4 beds

2 baths

$3,000

House for rent

10 Queen Elizabeth Court - Photo 1 of 1

4d ago

Condo for rent in Chester

Condo - CHESTER, MD

10 Queen Elizabeth Court, Chester, MD 21619

Swimming pool | Fitness center | Ceiling fan

1 bed

1 bath

$2,200

Condo 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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170 Harrier Way #22 - Photo 1 of 1

5d+ ago

Condo for rent in Chester

APARTMENT - Contemporary - CHESTER, MD

170 Harrier Way #22, Chester, MD 21619

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

2 beds

2 baths

$4,250

Condo for rent

1225 Seneca Road - Photo 1 of 1

5d+ ago

Apartment for rent in Bowleys Quarters

1225 Seneca Road, Bowleys Quarters, MD 21220

Air conditioning | Assigned parking | Central heat

1 bed

1 bath

$1,000

Apartment for rent

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Garage Parking

Storage

Hardwood Floor

In-Unit Laundry

804 Mason Road - Photo 1 of 1

5d+ ago

House for rent in Stevensville

804 Mason Road, Stevensville, MD 21666

In-unit laundry | Air conditioning | Assigned parking

2 beds

2 baths

$2,950

House for rent

214 Teal Ct Unit G #G - Photo 1 of 1

5d+ ago

Condo for rent in Chester

CONDOS - Colonial - CHESTER, MD

214 Teal Ct Unit G #G, Chester, MD 21619

In-unit laundry | Balcony | Walk-in closets

2 beds

2 baths

$2,150

Condo for rent

104 Laura Ln - Photo 1 of 1

5d+ ago

Apartment for rent in Galena

104 Laura Ln, Galena, MD 21635

Air conditioning | Assigned parking | Central heat

3 beds

2 baths

$2,000

Apartment for rent

5785 Downey Avenue - Photo 1 of 1

5d+ ago

House for rent in Rock Hall

5785 Downey Avenue, Rock Hall, MD 21661

In-unit laundry | Carpet

2 beds

1 bath

$1,400

House for rent

Available Nov 15

6119 New St Unit 2 #2 - Photo 1 of 1

5d+ ago

Condo for rent in Rock Hall

CONDOS - Contemporary - ROCK HALL, MD

6119 New St Unit 2 #2, Rock Hall, MD 21661

In-unit laundry | Garage parking | Hardwood floor

3 beds

3 baths

$3,800

Condo for rent

203 Romancoke Rd - Photo 1 of 1

5d+ ago

House for rent in Stevensville

Commercial/Industrial - STEVENSVILLE, MD

203 Romancoke Rd, Stevensville, MD 21666

Assigned parking | Business center

Studio

0 baths

$800

House for rent

Find sweet deals near Chestertown

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

102 Saint Claire Pl - Photo 1 of 1

5d+ ago

House for rent in Stevensville

Commercial/Industrial - STEVENSVILLE, MD

102 Saint Claire Pl, Stevensville, MD 21666

Air conditioning | Hardwood floor | Elevator

Studio

0 baths

$5,500

House for rent

28470 Lambs Meadow Road - Photo 1 of 1

20h ago

House for rent in Kennedyville

28470 Lambs Meadow Rd

28470 Lambs Meadow Road, Kennedyville, MD 21645

In-unit laundry | On-site laundry | Fireplace

3 beds

2 baths

$2,000

House for rent

Available Jan 1

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311 Holly Street #NA - Photo 1 of 1

5d+ ago

House for rent in Centreville

$1,800 - Charming 2 Bedroom 1 Bathroom Cottage In Centreville Heights With Great Amenities

311 Holly Street #NA, Centreville, MD 21617

In-unit laundry | Air conditioning | Hardwood floor

2 beds

1 bath

$1,800

House for rent

Available Jan 1

Bay Manor- Residential - Photo 1 of 1

3d ago

8.6

Very good

Bay Manor- Residential

214 Pier One Road, Stevensville, MD 21666

In-unit laundry | Air conditioning | Balcony

Studio–2 beds

1–2 baths

$1,900–$3,100

Condo for rent

815 Seneca Park Road - Photo 1 of 1
3D tour

4d ago

House for rent in Bowleys Quarters

5 beds

2 baths

$2,695

House for rent

3922 Cutty Sark Road - Photo 1 of 1

5d+ ago

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At Last, This Is What You Have Been Searching For!

3922 Cutty Sark Road, Bowleys Quarters, MD 21220

3 beds

1 bath

$1,865

House for rent

WW2120C - Photo 1 of 1

5d+ ago

9.1

Excellent

WW2120C

2120 Cedar Dr, Edgewood, MD 21040

Dishwasher | Oven

4 beds

2 baths

$1,395

Apartment for rent

11415 Eastern Avenue - Photo 1 of 1

3h ago

House for rent in Middle River

11415 Eastern Avenue, Middle River, MD 21220

In-unit laundry | On-site laundry | Dishwasher

3 beds

2 baths

$4,000

House for rent

402 Redbridge Street - Photo 1 of 1

3d ago

Townhouse for rent in Middle River

TOWNHOME - Other - MIDDLE RIVER, MD

402 Redbridge Street, Middle River, MD 21220

In-unit laundry | Garage parking | Swimming pool

4 beds

3 baths

$3,600

House for rent

Showing 1 - 25 of 25 results
Home > Apartments in Chestertown
Updated: December 16, 2025

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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 1040 square feet. The average size of a 3 bedroom apartment rental in Chestertown is 1476 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 deal203 Romancoke Rd
Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos