Show the map
Get to know
Chestertown
2
APARTMENTS
Rent Trends for Apartments in Chestertown
September 2025
| Bedroom count | Chestertown | vs Last Month |
|---|---|---|
| Studio | $1,350 | — |
| 1 Bedroom | $2,200 | — |
| 2 Bedroom | $2,000 |  down 17.53% |
Median rent as of September 7, 2025
This September, we've analyzed our 2 listings in Chestertown to determine the rent trend. We're updating our tables in real time to give you the most up to date Chestertown median apartment rent prices by bedroom count.
Cities Near Chestertown
Apartment Types in Chestertown
Find Your Dream Apartment for Rent in Chestertown
PadMapper has 2 condos, houses, and apartments for rent in Chestertown. Specifically, studio apartments, one-bedroom apartments, 1 two-bedroom apartments, three-bedroom apartments are currently available for rent.
We have options to filter by price, bedroom count, bathroom count, long-term or short-term, housing type, pet friendly, no broker fee, and you can search for an apartment by custom keywords.
Chestertown MD Apartments for Rent
Rent
Edit
Length
Bedrooms
Save
More Filters
$3,600
4 Bedrooms · 2 Bathrooms Apartment · Chestertown, MD
5+ Days Ago
Brices Mill Rd #0000 is a 4 bedroom, 2 bathrooms apartment for rent. It is located in Chestertown. It has apartment amenities including on-site management, and garage parking. View apartment
$2,500
2 Bedrooms · 1 Bathroom Apartment · Chestertown, MD
5+ Days Ago
202 High St #A is a 2 bedroom, 1 bathroom apartment for rent. It is located in Chestertown. View apartment
$2,600
3 Bedrooms · 2 Bathrooms Apartment · Queenstown, MD
2 Days Ago
249 Thompson Ave is a 3 bedroom, 2 bathrooms apartment for rent. It is located in Queenstown. It has apartment amenities including garage parking, and outdoor space. Cats and dogs are allowed, making it a pet-friendly apartment. View apartment
$2,400
3 Bedrooms · 2 Bathrooms Apartment · Greensboro, MD
3 Days Ago
104 Roe St is a 3 bedroom, 2 bathrooms apartment for rent. It is located in Greensboro. It has apartment amenities including outdoor space. View apartment
Online tours
$2,700
2 Bedrooms · 2 Bathrooms Apartment · Chester, MD
5+ Days Ago
54 Queen Caroline Ct is a 2 bedroom, 2 bathrooms apartment for rent. It is located in Chester. It has apartment amenities including outdoor space, swimming pool, and fitness center. View apartment
$3,000
2 Bedrooms · 1 Bathroom Apartment · Stevensville, MD
5+ Days Ago
2620 Love Point Rd is a 2 bedroom, 1 bathroom apartment for rent. It is located in Stevensville. View apartment
$3,500
4 Bedrooms · 3 Bathrooms Apartment · Stevensville, MD
5+ Days Ago
247 Jessica Lyn Ave is a 4 bedroom, 3 bathrooms apartment for rent. It is located in Stevensville. It has apartment amenities including garage parking, swimming pool, and on-site laundry. Cats and dogs are allowed, making it a pet-friendly apartment. View apartment
$600
Studio Apartment · Chester, MD
5+ Days Ago
1712 Main St is a studio, 0 bathrooms apartment for rent. It is located in Chester. View apartment
$5,500
Studio Apartment · Stevensville, MD
5+ Days Ago
102 Saint Claire Pl is a studio, 0 bathrooms apartment for rent. It is located in Stevensville. It has apartment amenities including elevator. View apartment
$1,400
Studio Apartment · Stevensville, MD
5+ Days Ago
203 Romancoke Rd is a studio, 0 bathrooms apartment for rent. It is located in Stevensville. It has apartment amenities including business center. View apartment
$2,400
3 Bedrooms · 2 Bathrooms Apartment · Bowleys Quarters, Bowleys Quarters
1 Day Ago
645 Nollmeyer Rd #645 is a 3 bedroom, 2 bathrooms apartment for rent. It is located in the Bowleys Quarters neighborhood of Bowleys Quarters. Cats and dogs are allowed, making it a pet-friendly apartment. View apartment
$3,300
3 Bedrooms · 2 Bathrooms Apartment · Essex, Essex
2 Days Ago
2209 Monocacy Rd is a 3 bedroom, 2 bathrooms apartment for rent. It is located in the Essex neighborhood of Essex. It has apartment amenities including outdoor space. View apartment
$2,600
4 Bedrooms · 2 Bathrooms Apartment · Joppatowne, Joppatowne
2 Days Ago
301 Stillmeadow Dr is a 4 bedroom, 2 bathrooms apartment for rent. It is located in the Joppatowne neighborhood of Joppatowne. It has apartment amenities including garage parking, outdoor space, and on-site laundry. View apartment
$2,895
4 Bedrooms · 2 Bathrooms Apartment · Edgewood, Edgewood
3 Days Ago
2605 Maidens Ln is a 4 bedroom, 2 bathrooms apartment for rent. It is located in the Edgewood neighborhood of Edgewood. It has apartment amenities including garage parking, and outdoor space. View apartment
$4,200
3 Bedrooms · 2 Bathrooms Apartment · Bowleys Quarters, Bowleys Quarters
3 Days Ago
3622 Claires Ln is a 3 bedroom, 2 bathrooms apartment for rent. It is located in the Bowleys Quarters neighborhood of Bowleys Quarters. It has apartment amenities including garage parking, storage, and on-site laundry. View apartment
$2,350
3 Bedrooms · 1 Bathroom Apartment · Grasonville, MD
4 Days Ago
112 Station Ln is a 3 bedroom, 1 bathroom apartment for rent. It is located in Grasonville. It has apartment amenities including garage parking, and outdoor space. View apartment
$2,195
5 Bedrooms · 2 Bathrooms Apartment · Edgewood, Edgewood
5+ Days Ago
1885 Brookside Dr is a 5 bedroom, 2 bathrooms apartment for rent. It is located in the Edgewood neighborhood of Edgewood. It has apartment amenities including outdoor space. View apartment
$2,000
2 Bedrooms · 1 Bathroom Apartment · Essex, Essex
4 Days Ago
2412 Poplar Rd is a 2 bedroom, 1 bathroom apartment for rent. It is located in the Essex neighborhood of Essex. It has apartment amenities including storage, outdoor space, and on-site laundry. View apartment
$1,195
3 Bedrooms · 1 Bathroom Apartment · Edgewood, Edgewood
5+ Days Ago
6203 Edgewood Rd #C is a 3 bedroom, 1 bathroom apartment for rent. It is located in the Edgewood neighborhood of Edgewood. View apartment
$2,200
3 Bedrooms · 1 Bathroom Apartment · Bowleys Quarters, Bowleys Quarters
5+ Days Ago
4032 Rustico Rd is a 3 bedroom, 1 bathroom apartment for rent. It is located in the Bowleys Quarters neighborhood of Bowleys Quarters. It has apartment amenities including outdoor space, storage, and on-site laundry. View apartment
That's All Folks!
We’re out of listings matching your filters. Want more results?
Modify Filters or Start a New Search