600 Perrys Corner Rd
GrasonvilleMD21638
Apartments for Rent in Chestertown, MD (91 Rentals) Page 2 of 2
110 Greybull Ln
GrasonvilleMD21638
202 Golden Eagle Way
BelcampMD21017
210 Trails Way
JoppatowneMD21085
671 Beadlilly Wy
JoppatowneMD21085
225 Joppa Farm Rd
JoppatowneMD21085
9135 Cuckold Point Rd
Sparrows PointMD21219
321 Piney Narrows Rd
ChesterMD21619
215 Kingfisher Ln
ChesterMD21619
30 Flaxleaf Ct
EssexMD21221
2513 Barrison Point Rd
EssexMD21221
6407 Falconwood St
Middle RiverMD21220
1419 Onnesta Ct
AberdeenMD21001
506 Ladywell St
BaltimoreMD21220
2922 Waterfront way
BaltimoreMD21230
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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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Studio to 2 Bedroom Apartments
425 High St
425 High StChestertown, MD 21620
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2 to 3 Bedroom Apartments
Ridgeview Court Apartments
400 Hadaway DrChestertown, 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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1 to 3 Bedroom Apartments
Magnolia Farms
28 E Bel Air AveAberdeen, 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 51-91, 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 | $1,081 | $937 | $1,255 |
| Chestertown 1 Bedroom Apartments | $1,626 | $765 | $2,356 |
| Chestertown 2 Bedroom Apartments | $1,767 | $950 | $2,991 |
| Chestertown 3 Bedroom Apartments | $2,021 | $1,050 | $2,924 |
| Chestertown 4 Bedroom Apartments | $2,185 | $1,979 | $2,400 |
How much does it cost to rent a home in Chestertown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| 2 Bedroom Homes | $1,730 | $1,500 | $2,000 |
| 3 Bedroom Homes | $2,521 | $1,195 | $5,000 |
| 4 Bedroom Homes | $3,472 | $2,700 | $4,300 |
| 5 Bedroom Homes | $4,266 | $3,800 | $4,500 |
| 6 Bedroom Homes | $2,300 | $2,300 | $2,300 |
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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, September 20, 2026, there are currently 91 available Chestertown apartments priced from $765 to $2,991, with an average monthly rent of $1,752.
How much are Studio apartments in Chestertown?
There are currently 7 Studio Apartments in Chestertown with rent ranges from $937 to $1,255 with an average price of $1,081.
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 $2,356 with an average monthly rent of $1,626.
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 $2,991. Today's average rental price for Two Bedrooms here is $1,767.
How expensive are Chestertown Three Bedroom Apartments?
There are currently 33 Three Bedroom Apartments listings available in Chestertown on ApartmentHomeLiving.com. The pricing ranges from $1,050 to $2,924 - averaging $2,021 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
How Commercial-to-Residential Property Conversions Help the Housing Crisis
Written by: Robin Stewart
Many housing markets throughout America share a common complaint: a lack of affordable rental properties.
Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
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Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
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.