Skip to navigationSkip to main contentSkip to footer
Zumper

Luxury Apartments for Rent in Chestertown, MD

25 rentals

104 Cedar St - Photo 1 of 1

5d+ ago

Luxury house for rent in Chestertown

SINGLE_FAMILY - Colonial - CHESTERTOWN, MD

104 Cedar St, Chestertown, MD 21620

Luxury | Garage parking | Ceiling fan

3 beds

2.5 baths

$2,600

House for rent

24731 Langford Rd #B - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Chestertown

Private country apartment

24731 Langford Rd #B, Chestertown, MD 21620

Luxury | In-unit laundry | On-site laundry

1 bed

1 bath

$1,200

Apartment for rent

Available Aug 15

Top amenities
Carpet
In-Unit Laundry
On-Site Laundry
Listings within 20 miles
212 Bohemia Church Rd - Photo 1 of 1

1h ago

Luxury house for rent in Warwick

212 Bohemia Church Rd, Warwick, MD 21912

Luxury | Balcony | In-unit laundry

3 beds

3 baths

$2,700

House for rent

Available Jul 1

Top amenities
Carpet
Dishwasher
Hardwood Floor
High Ceilings
In-Unit Laundry
Microwave
105 Dogwood Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Galena

SINGLE_FAMILY - Rambler - GALENA, MD

105 Dogwood Dr, Galena, MD 21635

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$2,500

House for rent

Top amenities
Ceiling Fan
Dishwasher
Garage Parking
In-Unit Laundry
705 Bayberry Rd - Photo 1 of 1

5d+ ago

Luxury Edgewood house for rent in Edgewood

SINGLE_FAMILY - Ranch - EDGEWOOD, MD

705 Bayberry Rd, Edgewood, MD 21040

Luxury | In-unit laundry | Hardwood floor

3 beds

1.5 baths

$2,600

House for rent

Top amenities
Ceiling Fan
In-Unit Laundry

Nearby rental good for eco-living

$2,695

Joppatowne

Nearby rental good for pet owners

1046 Agate Dr #1 - Photo 1 of 1

5d+ ago

Luxury Edgewood townhouse for rent in Edgewood

1046 Agate Drive - 1

1046 Agate Dr #1, Edgewood, MD 21040

Luxury | Balcony | Roof deck

4 beds

2.5 baths

$2,150

House for rent

Available Jun 1

Top amenities
Cable
Dishwasher
Hardwood Floor
Microwave
On-Site Laundry
Roof Deck
25 2nd Ave - Photo 1 of 1
New construction

4d ago

Luxury house for rent in Earleville

Detached, Single Family - EARLEVILLE, MD

25 2nd Ave, Earleville, MD 21919

Luxury | Outdoor space

3 beds

2 baths

$2,495

$2,395

Price drop

House for rent

2816 Profitt Path - Photo 1 of 1

5d+ ago

Luxury Edgewood house for rent in Edgewood

2816 Profitt Path, Edgewood, MD 21040

Luxury | In-unit laundry | On-site laundry

4 beds

3 baths

$2,950

House for rent

Available May 6

Top amenities
In-Unit Laundry
On-Site Laundry
The best of Zumper, delivered

Be the first to hear about new listings matching your search.

Email
By clicking submit, I accept Zumper's Terms and Conditions, Privacy Policy, and Community Values.
499 Berkshire Ct - Photo 1 of 1

5d+ ago

Luxury Joppatowne townhouse for rent in Joppatowne

4 Bedrooms 2.5 Bathrooms, Joppa MD

499 Berkshire Ct, Joppatowne, MD 21085

Luxury | Storage | Dishwasher

4 beds

2.5 baths

$2,200

House for rent

6209 Edgewood Rd #C - Photo 1 of 1

5d+ ago

Luxury Edgewood condo for rent in Edgewood

6209 Edgewood Rd #C, Edgewood, MD 21040

Luxury | Oven

2 beds

1 bath

$1,095

Condo for rent

Advertisement

Find sweet deals near Chestertown

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

$2,200

Joppatowne

$1,095

Edgewood

$1,250

Edgewood

$1,700

Edgewood

2842 Beckon Dr #1 - Photo 1 of 1

5d+ ago

Luxury Edgewood townhouse for rent in Edgewood

2842 Beckon Drive - 1

2842 Beckon Dr #1, Edgewood, MD 21040

Luxury | On-site laundry

4 beds

1.5 baths

$2,100

House for rent

Available May 1

Top amenities
On-Site Laundry
722 Church Hill Rd - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Centreville

SINGLE_FAMILY - National - CENTREVILLE, MD

722 Church Hill Rd, Centreville, MD 21617

Luxury | Hardwood floor | Ceiling fan

1 bed

1 bath

$1,400

Apartment for rent

Top amenities
Hardwood Floor
1703 Fountain Rock Way Unit B #1703B - Photo 1 of 1

5d+ ago

Luxury Edgewood condo for rent in Edgewood

CONDOS - Contemporary - EDGEWOOD, MD

1703 Fountain Rock Way Unit B #1703B, Edgewood, MD 21040

Luxury | In-unit laundry | Garage parking

2 beds

1 bath

$1,250

Condo for rent

Top amenities
Carpet
Dishwasher
In-Unit Laundry
2828 Beckon Dr - Photo 1 of 1

5d+ ago

Luxury Edgewood townhouse for rent in Edgewood

TOWNHOME - Other - EDGEWOOD, MD

2828 Beckon Dr, Edgewood, MD 21040

Luxury | In-unit laundry | On-site laundry

3 beds

2.5 baths

$2,300

House for rent

Top amenities
Assigned Parking
Ceiling Fan
Dishwasher
Hardwood Floor
In-Unit Laundry
On-Site Laundry
1501 Saint Christopher Ct - Photo 1 of 1

3d ago

Luxury Edgewood townhouse for rent in Edgewood

TOWNHOME - Colonial - EDGEWOOD, MD

1501 Saint Christopher Ct, Edgewood, MD 21040

Luxury | Walk-in closets | Air conditioning

4 beds

2 baths

$2,450

$2,200

Price drop

House for rent

1 Edgewood Road #1 - Photo 1 of 1

5d+ ago

Luxury Edgewood apartment for rent in Edgewood

4048 Edgewood Road - 1

1 Edgewood Road #1, Edgewood, MD 21040

Luxury

1 bed

1 bath

$1,150

Apartment for rent

Available Nov 26

905 Swallow Crest Ct #E - Photo 1 of 1

5d+ ago

Luxury Edgewood condo for rent in Edgewood

905 Swallow Crest Ct #E, Edgewood, MD 21040

Luxury | Swimming pool | Dishwasher

2 beds

1 bath

$1,495

Condo for rent

231 Joppa Farm Rd - Photo 1 of 1
New construction

5d+ ago

Luxury Joppatowne townhouse for rent in Joppatowne

TOWNHOME - Other - JOPPA, MD

231 Joppa Farm Rd, Joppatowne, MD 21085

Luxury | Walk-in closets | Fitness center

4 beds

3.5 baths

$3,200

House for rent

Top amenities
Dishwasher
High Ceilings
Advertisement
8 Lasonia Ct - Photo 1 of 1
3D tour

5d+ ago

Luxury Edgewood house for rent in Edgewood

8 Lasonia Ct/ Large 3 bedroom 2.5 bath house

8 Lasonia Ct, Edgewood, MD 21040

Luxury | Garage parking | On-site laundry

3 beds

3 baths

$2,195

House for rent

Top amenities
Carpet
Dishwasher
Garage Parking
On-Site Laundry
313 Winterberry Dr - Photo 1 of 1

5d+ ago

Luxury Edgewood house for rent in Edgewood

313 Winterberry Dr, Edgewood, MD 21040

Luxury

3 beds

2.5 baths

$2,095

House for rent

903 Woodbridge Ct #D - Photo 1 of 1

5d+ ago

Luxury Edgewood apartment for rent in Edgewood

903 Woodbridge Ct #D, Edgewood, MD 21040

Luxury | In-unit laundry | On-site laundry

2 beds

1 bath

$1,500

Apartment for rent

Available Jun 30

Top amenities
In-Unit Laundry
On-Site Laundry
512 Scholar Ct - Photo 1 of 1

5d+ ago

Luxury Edgewood townhouse for rent in Edgewood

512 Scholar Court Edgewood, Maryland 21040

512 Scholar Ct, Edgewood, MD 21040

Luxury | In-unit laundry | Air conditioning

3 beds

2.5 baths

$2,150

House for rent

Available Jul 1

Top amenities
Air Conditioning
In-Unit Laundry
On-Site Laundry
Storage
6207 Edgewood Rd #C - Photo 1 of 1

5d+ ago

Luxury Edgewood condo for rent in Edgewood

6207 Edgewood Rd #C, Edgewood, MD 21040

Luxury | Oven

3 beds

1 bath

$1,195

Condo for rent

1945 Graymount Way - Photo 1 of 1

5d+ ago

Luxury Edgewood townhouse for rent in Edgewood

1945 Graymount Way, Edgewood, MD 21040

Luxury | In-unit laundry | Air conditioning

3 beds

2 baths

$2,195

House for rent

Top amenities
Assigned Parking
Dishwasher
In-Unit Laundry
On-Site Laundry
313 Garnett Rd - Photo 1 of 1

5d+ ago

Luxury Joppatowne house for rent in Joppatowne

313 Garnett Rd, Joppatowne, MD 21085

Luxury | In-unit laundry | Air conditioning

4 beds

3 baths

$2,695

House for rent

Top amenities
Garage Parking
In-Unit Laundry
Showing 1 - 25 of 25 results
Home > Apartments in Chestertown > Chestertown Luxury Apartments For Rent
Updated: June 10, 2026

Are you a rental professional?

Try our tenant screening, or post rental listings to Zumper, Craigslist Chestertown, and more.
Atlanta ApartmentsAustin ApartmentsBaltimore ApartmentsBoston ApartmentsCharlotte ApartmentsChicago ApartmentsDallas ApartmentsDenver ApartmentsDetroit ApartmentsHouston ApartmentsLas Vegas ApartmentsLos Angeles ApartmentsMiami ApartmentsMinneapolis ApartmentsNew York ApartmentsPhiladelphia ApartmentsPhoenix ApartmentsPittsburgh ApartmentsPortland ApartmentsSan Antonio ApartmentsSan Diego ApartmentsSan Francisco ApartmentsSeattle ApartmentsTampa ApartmentsWashington DC Apartments

Looking for apartments in Chestertown, MD near you?

🔑Available apartment rentals25
💰Best rent deal24731 Langford Rd #B
✨Popular amenities, ,
🍽With dishwasher
🏠With photos

For more in depth rent prices, check out our Chestertown, MD rent data, which covers average and median rents in Chestertown, MD.

To know how much rent you can afford in Chestertown, MD, use our rent affordability calculator.

If you're looking for a specific type of apartment near Chestertown, MD, use our helpful filters to find an apartment you will love!