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Luxury Apartments for Rent in Chestertown, MD

25 rentals

229 N Kent St - Photo 1 of 1

2d ago

Luxury house for rent in Chestertown

Single Family, Other - CHESTERTOWN, MD

229 N Kent St, Chestertown, MD 21620

Luxury | In-unit laundry

2 beds

1 bath

$1,550

House for rent

Top amenities
In-Unit Laundry
517 High St #C - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Chestertown

2 Bed / 1 Bath Unit in Chestertown - $1575 - Available 02/01

517 High St #C, Chestertown, MD 21620

Luxury | In-unit laundry | Hardwood floor

2 beds

1 bath

$1,575

Apartment for rent

Available Feb 1

Top amenities
In-Unit Laundry
517 High St #B - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Chestertown

1 Bed, 1 Bath Unit on High St. in Chestertown - Available 2/1 - $1400/mo

517 High St #B, Chestertown, MD 21620

Luxury | Balcony | In-unit laundry

1 bed

1 bath

$1,400

Apartment for rent

Available Feb 1

Top amenities
Hardwood Floor
In-Unit Laundry
517 High St #A - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Chestertown

Studio Unit in Chestertown | 1 Bath | $900/mo | Available 2/1/2025

517 High St #A, Chestertown, MD 21620

Luxury | Balcony | In-unit laundry

Studio

1 bath

$900

Apartment for rent

Available Feb 1

Top amenities
In-Unit Laundry
On-Site Laundry
118 North Water Street #3 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Chestertown

118 North Water Street

118 North Water Street #3, Chestertown, MD 21620

Luxury | In-unit laundry | Hardwood floor

2 beds

1 bath

$1,400

Apartment for rent

Available Dec 15

Top amenities
In-Unit Laundry
129 Manor Avenue - Photo 1 of 1

5d+ ago

Luxury house for rent in Chestertown

3 Bedroom 2 Bath Rancher for Rent

129 Manor Avenue, Chestertown, MD 21620

Luxury | In-unit laundry | Garage parking

3 beds

2 baths

$2,000

House for rent

Available Jan 15

Top amenities
In-Unit Laundry

Nearby rental good for eco-living

$3,900

Bowleys Quarters

Nearby rental good for pet owners

Listings within 10 miles
10546 Worton Road - Photo 1 of 1

5d+ ago

Luxury house for rent in Worton

SINGLE_FAMILY - Ranch - WORTON, MD

10546 Worton Road, Worton, MD 21678

Luxury | Garage parking | Ceiling fan

4 beds

2 baths

$2,600

House for rent

501 Main Street #4-501 - Photo 1 of 1

5d+ ago

Luxury house for rent in Church Hill

SINGLE_FAMILY - Other - CHURCH HILL, MD

501 Main Street #4-501, Church Hill, MD 21623

Luxury

1 bed

1 bath

$1,250

House for rent

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106 Johnstown Lane #1 - Photo 1 of 1

5d+ ago

Luxury house for rent in Centreville

106 Johnstown Lane - 1

106 Johnstown Lane #1, Centreville, MD 21617

Luxury | In-unit laundry

3 beds

2 baths

$2,000

House for rent

Available Dec 1

Top amenities
In-Unit Laundry
5785 Downey Avenue - Photo 1 of 1

5d+ ago

Luxury house for rent in Rock Hall

5785 Downey Avenue, Rock Hall, MD 21661

Luxury | In-unit laundry | Carpet

2 beds

1 bath

$1,400

House for rent

Available Nov 15

Top amenities
In-Unit Laundry
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Find sweet deals near Chestertown

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

$2,150

Chester

$1,950

Stevensville

$1,865

Bowleys Quarters

$2,500

Chester

6119 New St Unit 2 #2 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Rock Hall

CONDOS - Contemporary - ROCK HALL, MD

6119 New St Unit 2 #2, Rock Hall, MD 21661

Luxury | Walk-in closets | In-unit laundry

3 beds

3 baths

$3,800

Condo for rent

Top amenities
Ceiling Fan
Fireplace
In-Unit Laundry
Storage
Listings within 20 miles
6627 Friels Rd - Photo 1 of 1

2d ago

Luxury house for rent in Queenstown

6627 Friels Rd

6627 Friels Rd, Queenstown, MD 21658

Luxury | Balcony | In-unit laundry

3 beds

2 baths

$2,650

House for rent

Available Mar 1

Top amenities
Dishwasher
In-Unit Laundry
Microwave
922 Petinot Pl - Photo 1 of 1

5d+ ago

Luxury house for rent in Stevensville

SINGLE_FAMILY - Other - STEVENSVILLE, MD

922 Petinot Pl, Stevensville, MD 21666

Luxury | Balcony | Walk-in closets

3 beds

2 baths

$2,800

House for rent

Top amenities
Ceiling Fan
Dishwasher
Fireplace
In-Unit Laundry
On-Site Laundry
444 Railroad Ave - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Centreville

TOWNHOME - National - CENTREVILLE, MD

444 Railroad Ave, Centreville, MD 21617

Luxury

2 beds

1 bath

$1,750

House for rent

10-B Queen Elizabeth Ct - Photo 1 of 1

5d+ ago

Luxury condo for rent in Chester

Condo - CHESTER, MD

10-B Queen Elizabeth Ct, Chester, MD 21619

Luxury | Swimming pool | Fitness center

1 bed

1 bath

$2,200

Condo for rent

Top amenities
Swimming Pool
170 Harrier Way #22 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Chester

APARTMENT - Contemporary - CHESTER, MD

170 Harrier Way #22, Chester, MD 21619

Luxury | Balcony | Swimming pool

2 beds

2 baths

$4,250

Condo for rent

Top amenities
Fitness Center
Garage Parking
In-Unit Laundry
On-Site Laundry
Swimming Pool
804 Mason Road - Photo 1 of 1

5d+ ago

Luxury house for rent in Stevensville

804 Mason Road, Stevensville, MD 21666

Luxury | Swimming pool | In-unit laundry

2 beds

2 baths

$2,950

House for rent

Top amenities
Assigned Parking
Dishwasher
In-Unit Laundry
Microwave
214 Teal Ct Unit G #G - Photo 1 of 1

5d+ ago

Luxury condo for rent in Chester

CONDOS - Colonial - CHESTER, MD

214 Teal Ct Unit G #G, Chester, MD 21619

Luxury | Balcony | Walk-in closets

2 beds

2 baths

$2,150

Condo for rent

Top amenities
In-Unit Laundry
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815 Seneca Park Rd - Photo 1 of 1
3D tour

5d+ ago

Luxury Bowleys Quarters house for rent in Bowleys Quarters

815 Seneca Park Rd, Bowleys Quarters, MD 21220

Luxury | Outdoor space | Oven

5 beds

2 baths

$2,695

House for rent

203 Romancoke Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Stevensville

Commercial/Industrial - STEVENSVILLE, MD

203 Romancoke Rd, Stevensville, MD 21666

Luxury | Assigned parking | Business center

Studio

0 baths

$800

House for rent

102 Saint Claire Pl - Photo 1 of 1

5d+ ago

Luxury house for rent in Stevensville

Commercial/Industrial - STEVENSVILLE, MD

102 Saint Claire Pl, Stevensville, MD 21666

Luxury | Air conditioning | Hardwood floor

Studio

0 baths

$5,500

House for rent

Bay Manor- Residential - Photo 1 of 1

2d ago

8.6

Very good

Bay Manor- Residential

214 Pier 1 Rd, Stevensville, MD 21666

Luxury | Balcony | Roof deck

Studio–2 beds

1–2 baths

$1,950–$3,100

Condo for rent

Top amenities
Air Conditioning
Elevator
Hardwood Floor
In-Unit Laundry
Microwave
Package Service
3922 Cutty Sark Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

At Last, This Is What You Have Been Searching For!

3922 Cutty Sark Rd, Bowleys Quarters, MD 21220

Luxury

3 beds

1 bath

$1,865

House for rent

WW2120C - Photo 1 of 1

4d ago

9.1

Excellent

WW2120C

2120 Cedar Dr, Edgewood, MD 21040

Luxury | Dishwasher | Oven

4 beds

2 baths

$1,395

Apartment for rent

Explore surrounding listings that match your search:
601 Colindale St - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Middle River

TOWNHOME - Craftsman - MIDDLE RIVER, MD

601 Colindale St, Middle River, MD 21220

Luxury | Swimming pool | Fitness center

4 beds

3 baths

$2,800

House for rent

Top amenities
Dishwasher
Fitness Center
In-Unit Laundry
Swimming Pool
Showing 1 - 25 of 25 results
Home > Apartments in Chestertown > Chestertown Luxury Apartments For Rent
Updated: January 5, 2026

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Looking for apartments in Chestertown, MD near you?

🔑Available apartment rentals25
💰Best rent deal517 High St #A
✨Popular amenities, ,
🏠With photos

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