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Apartments for Rent in Chestertown, MD

Average rent

$1,650
increased by45%

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202 High St #E - Photo 1 of 1

1d 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

129A Manor Ave - Photo 1 of 1

4d ago

House for rent in Chestertown

3 Bedroom 2 Bath Rancher for Rent

129A Manor Ave, 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.

517 High St #C - Photo 1 of 1

5d+ ago

Apartment for rent in Chestertown

2 Bed / 1 Bath Unit in Chestertown - $1575 - Available 02/01

517 High St #C, Chestertown, MD 21620

In-unit laundry | Hardwood floor | Outdoor space

2 beds

1 bath

$1,575

Apartment for rent

Available Feb 1

Charming Apartment with Shared Outdoor Space

This spacious 2-bedroom, 1-bath apartment on the second floor boasts attractive architectural details and abundant natural light. Enjoy a shared deck, fenced yard, and welcoming front porch, all within minutes of downtown shops and parks. A perfect blend of comfort and convenience, ideal for pet lovers. Rent includes common area maintenance; utilities are tenants' responsibility. Available for $1,575 starting February 2026.

Listings within 10 miles
11149 Old Worton Rd - Photo 1 of 1

5d+ ago

Apartment for rent in Worton

APARTMENT - Other - WORTON, MD

11149 Old Worton Rd, Worton, MD 21678

In-unit laundry | Ceiling fan | Outdoor space

3 beds

1 bath

$1,600

Apartment for rent

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

$3,500

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

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

720 Church Hill Rd - Photo 1 of 1

3d 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

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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

5785 Downey Ave - Photo 1 of 1

5d+ ago

House for rent in Rock Hall

5785 Downey Ave, Rock Hall, MD 21661

In-unit laundry | Carpet

2 beds

1 bath

$1,400

House for rent

Available Nov 15

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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

Listings within 20 miles
273 Thompson Ave - Photo 1 of 1

1d ago

Townhouse for rent in Queenstown

273 Thompson Ave, Queenstown, MD 21658

In-unit laundry | Assigned parking | Central heat

3 beds

2 baths

$2,600

House for rent

Available Mar 15

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

25-E Queen Elizabeth Ct - Photo 1 of 1

5d+ ago

Condo for rent in Chester

CONDOS - Loft, Spanish - CHESTER, MD

25-E Queen Elizabeth Ct, Chester, MD 21619

In-unit laundry | Swimming pool | Fitness center

2 beds

2 baths

$2,800

Condo for rent

Find sweet deals near Chestertown

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

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

922 Petinot Pl - Photo 1 of 1

5d+ ago

House for rent in Stevensville

SINGLE_FAMILY - Other - STEVENSVILLE, MD

922 Petinot Pl, Stevensville, MD 21666

In-unit laundry | On-site laundry | Balcony

3 beds

2 baths

$2,800

House for rent

444 Railroad Ave - Photo 1 of 1

5d+ ago

Townhouse for rent in Centreville

TOWNHOME - National - CENTREVILLE, MD

444 Railroad Ave, Centreville, MD 21617

2 beds

1 bath

$1,650

House for rent

170 Harrier Way Unit 22 #22 - Photo 1 of 1

5d+ ago

Condo for rent in Chester

APARTMENT - Contemporary - CHESTER, MD

170 Harrier Way Unit 22 #22, Chester, MD 21619

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

2 beds

2 baths

$4,250

Condo for rent

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

5d+ ago

House for rent in Bowleys Quarters

5 beds

2 baths

$2,490

House for rent

269 Thompson Ave - Photo 1 of 1

1d ago

Townhouse for rent in Queenstown

269 Thompson Ave

269 Thompson Ave, Queenstown, MD 21658

In-unit laundry | Garage parking | Carpet

3 beds

2 baths

$2,600

House for rent

Available Mar 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

$3,495

House for rent

Available Feb 14

Bay Manor- Residential - Photo 1 of 1

12h 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–$3,100

Condo for rent

3922 Cutty Sark Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

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

3922 Cutty Sark Rd, Bowleys Quarters, MD 21220

3 beds

1 bath

$1,860

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

6 Maryland Ave #6B - Photo 1 of 1
New construction

1d ago

House for rent in Ridgely

6 Maryland Ave

6 Maryland Ave #6B, Ridgely, MD 21660

In-unit laundry | On-site laundry | Outdoor space

4 beds

2 baths

$2,450

House for rent

Showing 1 - 25 of 25 results
Home > Apartments in Chestertown
Updated: February 4, 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 1 bedroom apartment rental in Chestertown is 520 square feet. The average size of a 2 bedroom apartment rental in Chestertown is 347 square feet. The average size of a 3 bedroom apartment rental in Chestertown is 960 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 deal517 High St #C
Popular amenities, ,
🏠With photos