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5d+ ago
House for rent in Chestertown
222 Mount Vernon Ave #NA, Chestertown, MD 21620
Assigned parking | Hardwood floor | Walk-in closets
4 beds
2 baths
$2,950
$2,600
Price drop
House for rent
Available Jul 1
5d+ ago
House for rent in Chestertown
Cedar Point Rd #NA, Chestertown, MD 21620
Garage parking | On-site laundry | Assigned parking
3 beds
1 bath
$1,900
House for rent
Available Sep 6
5d+ ago
House for rent in Chestertown
129A Manor Ave, Chestertown, MD 21620
In-unit laundry | Garage parking | Storage
3 beds
2 baths
$2,000
House for rent
Available Jul 15
5d+ ago
Townhouse for rent in Chestertown
3 beds
1 bath
$2,000
House for rent
5d+ ago
House for rent in Chestertown
8890 Fairlee Rd, Chestertown, MD 21620
In-unit laundry | On-site laundry | Hardwood floor
3 beds
2 baths
$2,500
House for rent
1d ago
House for rent in Stevensville
2620 Love Point Rd, Stevensville, MD 21666
In-unit laundry | Furnished | Ceiling fan
5 beds
5 baths
$5,000
House for rent
5d+ ago
Townhouse for rent in Centreville
2 beds
1 bath
$1,650
House for rent
5d+ ago
House for rent in Centreville
116 Walnut St, Centreville, MD 21617
Air conditioning | Hardwood floor | Storage
3 beds
1 bath
$2,250
House for rent
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1d ago
House for rent in Edgewood
3 beds
2 baths
$1,900
House for rent
5d+ ago
House for rent in Queenstown
3 beds
1 bath
$2,400
House for rent
5d+ ago
Condo for rent in Chester
190 Harrier Way #24, Chester, MD 21619
In-unit laundry | Garage parking | Balcony
3 beds
2.5 baths
$4,000
Condo for rent
5d+ ago
Condo for rent in Edgewood
3 beds
1 bath
$1,495
Condo for rent
5d+ ago
Condo for rent in Edgewood
3 beds
1 bath
$1,195
Condo for rent
5d+ ago
Townhouse for rent in Edgewood
3 beds
2 baths
$1,999
House for rent
5d+ ago
House for rent in Edgewood
1322 Harford Square Dr #NA, Edgewood, MD 21040
In-unit laundry | Air conditioning | Assigned parking
3 beds
3 baths
$2,300
House for rent
Available Jul 15
These rentals are 10%-30% cheaper than the local average price for similar rentals.
1d ago
House for rent in Centreville
119 Watson Rd, Centreville, MD 21617
Furnished | On-site laundry | Hardwood floor
4 beds
3 baths
$4,300
House for rent
5d+ ago
House for rent in Centreville
212 Frederick Dr, Centreville, MD 21617
In-unit laundry | Garage parking | Walk-in closets
4 beds
2.5 baths
$2,890
House for rent
5d+ ago
House for rent in Chester
137 Warbler Way, Chester, MD 21619
In-unit laundry | Garage parking | Swimming pool
2 beds
2 baths
$4,300
House for rent
5d+ ago
Townhouse for rent in Edgewood
2842 Beckon Dr, Edgewood, MD 21040
In-unit laundry | Fitness center | Ceiling fan
4 beds
2 baths
$2,100
House for rent
5d+ ago
Townhouse for rent in Edgewood
3 beds
1 bath
$1,945
$1,745
Price drop
House for rent
5d+ ago
Apartment for rent in Edgewood
Air conditioning | On-site laundry | Assigned parking
2 beds
1 bath
$1,250
Apartment for rent
5d+ ago
Condo for rent in Edgewood
807 Windstream Way Unit C #807C, Edgewood, MD 21040
In-unit laundry | Garage parking | Storage
3 beds
1.5 baths
$1,700
Condo for rent
5d+ ago
Townhouse for rent in Edgewood
3 beds
1.5 baths
$1,995
House for rent
4d ago
House for rent in Edgewood
705 Bayberry Rd, Edgewood, MD 21040
In-unit laundry | Hardwood floor | Ceiling fan
3 beds
1.5 baths
$2,400
House for rent
5d+ ago
Condo for rent in Edgewood
2 beds
1 bath
$1,650
Condo for rent
Available Jul 21
Average rent
The average rent in Chestertown, as of July 2026, is up 8.04% compared to last month but down 13.45% year-over-year.Track prices
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52 rentals
6 rentals
17 rentals
8 rentals
8 rentals
6 rentals
27 rentals
14 rentals
7 rentals
10 rentals
14 rentals
11 rentals
5 rentals
83 rentals
8 rentals
27 rentals
7 rentals
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28 rentals
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 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.
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.
The average size of a 1 bedroom apartment rental in Chestertown is 790 square feet. 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 1465 square feet.
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.
| 🔑Available apartment rentals | 25 |
|---|---|
| 💰Best rent deal | Cedar Point Rd #NA |
| ✨Popular amenities | , , |
| 🧦In-unit laundry | |
| 🍽With dishwasher | |
| 🏠With photos |