1347 Harford Square Dr
EdgewoodMD21040
Apartments for Rent in Chestertown, MD (97 Rentals) Page 2 of 2
2842 Beckon Dr
EdgewoodMD21040
1424 St Michael Ct
EdgewoodMD21040
556 Burlington Ct
EdgewoodMD21040
1473 Charlestown Dr
EdgewoodMD21040
705 Bayberry Rd
EdgewoodMD21040
600 Perrys Corner Rd
GrasonvilleMD21638
80 Longbow Ln
HartlyDE19953
702 Towne Center Dr
JoppatowneMD21085
209 Bridge Dr
JoppatowneMD21085
2939 Shaws Rd
Sparrows PointMD21219
9135 Cuckold Point Rd
Sparrows PointMD21219
41A Queen Catherine Ct
ChesterMD21619
1806 Middleborough Rd
EssexMD21221
2513 Barrison Point Rd
EssexMD21221
12299 Eastern Ave
Middle RiverMD21220
1137 SPLASHING Dr
AbingdonMD21009
70 Swan St
AberdeenMD21001
99 Liberty St
AberdeenMD21001
4927 Bristle Cone Cir
AberdeenMD21001
1419 Onnesta Ct
AberdeenMD21001
627 Davol Rd
StevensvilleMD21666
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2 to 3 Bedroom Apartments
8221-8223 Tolchester Rd
8221-8223 Tolchester RdChestertown, MD 21620
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3 Bedroom Apartments
The Village at Chestertown
235 Island Lark WayChestertown, MD 21620
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1 to 2 Bedroom Apartments
121 Washington Ave
121 Washington AveChestertown, MD 21620
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Studio Apartments
Upper Shore Aging
402 Morgnec RdChestertown, MD 21620
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1 to 3 Bedroom Apartments
200 N Queen St
200 N Queen StChestertown, MD 21620
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2 Bedroom Apartments
104 Maple Ave
104 Maple AveChestertown, MD 21620
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2 to 3 Bedroom Apartments
Ridgeview Court Apartments
400 Hadaway DrChestertown, MD 21620
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Studio to 2 Bedroom Apartments
425 High St
425 High StChestertown, MD 21620
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1 Bedroom Apartments
321 Calvert St
321 Calvert StChestertown, MD 21620
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1 Bedroom Apartments
187 Flatland Rd
187 Flatland RdChestertown, MD 21620
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1 to 4 Bedroom Apartments
Baywood Village
23160-23165 Baywood CtChestertown, MD 21620
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1 to 2 Bedroom Apartments
Brookmeadow Apartments
150-160 Flatland RdChestertown, MD 21620
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2 to 3 Bedroom Apartments
Calvert Heights Townhouse Apartments
103 Hawkins DrChestertown, MD 21620
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1 to 3 Bedroom Apartments
Chestertown Cove Apartments
408 Morgnec RdChestertown, MD 21620
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1 to 3 Bedroom Apartments
Chestertown Landing
100 Schooner WayChestertown, MD 21620
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1 to 3 Bedroom Apartments
Center Park Apartments
38 Center ParkCentreville, MD 21617
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1 to 2 Bedroom Apartments
The Village at Slippery Hill Senior Apartments- 62+
320 Fallen Horse CirQueenstown, MD 21658
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1 to 2 Bedroom Apartments
Brookside Station Apartments
1618 Swallow Crest DrEdgewood, MD 21040
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1 to 2 Bedroom Apartments
Edgewood Park Apartments
611 Edgewood RdEdgewood, MD 21040
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1 to 2 Bedroom Apartments
Merion Village
904 Edgewood RdEdgewood, MD 21040
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1 to 2 Bedroom Apartments
Chesapeake Village Apartments
227 Carroll Island RdMiddle River, MD 21220
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1 to 3 Bedroom Apartments
Stansbury Manor
1 Alder DrMiddle River, MD 21220
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1 to 2 Bedroom Apartments
Perryman Station Senior Apartments, 62+
1222 Perryman RdAberdeen, MD 21001
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3 Bedroom Apartments
Winston's Choice Family Townhomes
59 Taft StAberdeen, MD 21001
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1 to 3 Bedroom Apartments
Holly Circle Townhouses
686 Holly CirAberdeen, MD 21001
Showing Results 51-97, Page 2 of 2
Chestertown, MD Local Guide
How much does it cost to rent an apartment in Chestertown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chestertown Studio Apartments | $1,149 | $897 | $1,706 |
| Chestertown 1 Bedroom Apartments | $1,596 | $765 | $2,256 |
| Chestertown 2 Bedroom Apartments | $1,695 | $950 | $2,855 |
| Chestertown 3 Bedroom Apartments | $1,986 | $1,050 | $3,523 |
| Chestertown 4 Bedroom Apartments | $2,180 | $2,009 | $2,345 |
How much does it cost to rent a home in Chestertown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| 2 Bedroom Homes | $1,645 | $1,095 | $2,300 |
| 3 Bedroom Homes | $2,204 | $1,195 | $3,600 |
| 4 Bedroom Homes | $2,972 | $1,900 | $4,300 |
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Frequently Asked Questions about Chestertown
What is the current pricing and availability for apartments for rent in Chestertown, MD?
As of today, August 06, 2026, there are currently 97 available Chestertown apartments priced from $765 to $3,523, with an average monthly rent of $1,705.
What Chestertown neighborhoods have the most available apartments?
There are 1 neighborhoods in the Chestertown area with available listings as of today. The three neighborhoods with the most options are Miramar Landing - Gibson/Taylor with 95 listings, Miramar Landing - Woodfield/Wyngate with 95 listings, and Middle River Baltimore Crossroads with 96 listings.
How much are Studio apartments in Chestertown?
There are currently 7 Studio Apartments in Chestertown with rent ranges from $897 to $1,706 with an average price of $1,149.
What is the current price range for One Bedroom Chestertown Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Chestertown ranges from $765 to $2,256 with an average monthly rent of $1,596.
What does renting a Two Bedroom Apartment in Chestertown cost?
The monthly rent prices of Two Bedroom Apartments currently available in Chestertown range from $950 to $2,855. Today's average rental price for Two Bedrooms here is $1,695.
How expensive are Chestertown Three Bedroom Apartments?
There are currently 32 Three Bedroom Apartments listings available in Chestertown on ApartmentHomeLiving.com. The pricing ranges from $1,050 to $3,523 - averaging $1,986 for the location.
Expert Rental Resources
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Articles, How-To's, and Tips
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.
Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.